Citation: Zhong Jun LI, He Qing HUANG, Meng Shen CAI. STEREOSELECTIVE AND MILD METHOD FOR THE SYNTHESIS OF α-D-MANNOPYRANOSIDES AND RELATED OLIGOSACCHARIDES IN HIGH YIELD[J]. Chinese Chemical Letters, ;1994, 5(6): 477-480. shu

STEREOSELECTIVE AND MILD METHOD FOR THE SYNTHESIS OF α-D-MANNOPYRANOSIDES AND RELATED OLIGOSACCHARIDES IN HIGH YIELD

School of Pharmaceutical Sciences, Beijing Medical University, Beijing 100083

Received Date: 29 March 1994

Model reaction of 1-O-(3,5-dinitrobenzoyl)-2,3,4,6-tetra-O-benzyl-α-D-mannopyranose 1 with a series of carboxylic acids,phenols,alcohols and saccharides respectively demonstrated that stereocontrolled mannosyl transfer with the retention of configuration at the anomeric center was best carried out in dichloromethane (-20℃→r.t.) with TMSOTf as the Lewis acid catalyst,DBMP as a deprotic agent and powdered 3A molecular sieves as a desiccating agent.Under these conditions,α-D-mannopyranosides and related oligosaccharides were obtained in good yields.
1. [1]
  Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
2. [2]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
3. [3]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
4. [4]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
5. [5]
  Liwen Wang , Boyang Wang , Siyu Lu , Shubo Lv , Xiaoli Qu . High quantum yield yellow emission carbon dots for the construction of blue light blocking films. Chinese Chemical Letters, 2025, 36(2): 110497-. doi: 10.1016/j.cclet.2024.110497
6. [6]
  Shuying Li , Weiwei ZhuGe , Xuan Sun , Chongzhen Sun , Zhaojun Liu , Chenghe Xiong , Min Xiao , Guofeng Gu . Convergent synthesis and immunological study of oligosaccharide derivatives related to galactomannan from Antrodia cinnamomea. Chinese Chemical Letters, 2024, 35(5): 109089-. doi: 10.1016/j.cclet.2023.109089
7. [7]
  Wenxuan Yang , Long Shang , Xiaomeng Liu , Sihan Zhang , Haixia Li , Zhenhua Yan , Jun Chen . Ultrafast synthesis of nanocrystalline spinel oxides by Joule-heating method. Chinese Chemical Letters, 2024, 35(11): 109501-. doi: 10.1016/j.cclet.2024.109501
8. [8]
  Xiao-Gang Wang , Ai-E Wang , Pei-Qiang Huang . Corrigendum to "A concise formal stereoselective total synthesis of (–)-swainsonine" [Chin Chem Lett 25 (2014) 193–196]. Chinese Chemical Letters, 2025, 36(3): 110597-. doi: 10.1016/j.cclet.2024.110597
9. [9]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974
10. [10]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
11. [11]
  Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
12. [12]
  Yihong Li , Zhong Qiu , Lei Huang , Shenghui Shen , Ping Liu , Haomiao Zhang , Feng Cao , Xinping He , Jun Zhang , Yang Xia , Xinqi Liang , Chen Wang , Wangjun Wan , Yongqi Zhang , Minghua Chen , Wenkui Zhang , Hui Huang , Yongping Gan , Xinhui Xia . Plasma enhanced reduction method for synthesis of reduced graphene oxide fiber/Si anode with improved performance. Chinese Chemical Letters, 2024, 35(11): 109510-. doi: 10.1016/j.cclet.2024.109510
13. [13]
  Jing Guo , Zhi-Guo Lu , Rui-Chen Zhao , Bao-Ku Li , Xin Zhang . Nucleic acid therapy for metabolic-related diseases. Chinese Chemical Letters, 2025, 36(3): 109875-. doi: 10.1016/j.cclet.2024.109875
14. [14]
  Jinwei Zhang , Lipiao Bao , Xing Lu . Synthesis methodologies of conductive 2D conjugated metal-organic frameworks. Chinese Journal of Structural Chemistry, 2025, 44(4): 100459-100459. doi: 10.1016/j.cjsc.2024.100459
15. [15]
  Gaojie Zhu , Zhen Yang , Shijun Li , Weihua Zhu , Rui Cao , Junlong Zhang , Jianzhang Zhao , Jonathan L. Sessler , Xunjin Zhu , Jianxin Song , Yongshu Xie , Jianzhuang Jiang . The 2^nd Asian Conference on Porphyrins, Phthalocyanines and Related Materials. Chinese Chemical Letters, 2024, 35(7): 109535-. doi: 10.1016/j.cclet.2024.109535
16. [16]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
17. [17]
  Huanyan Liu , Jiajun Long , Hua Yu , Shichao Zhang , Wenbo Liu . Rational design of highly conductive and stable 3D flexible composite current collector for high performance lithium-ion battery electrodes. Chinese Chemical Letters, 2025, 36(3): 109712-. doi: 10.1016/j.cclet.2024.109712
18. [18]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
19. [19]
  Rui Cheng , Tingting Zhang , Xin Huang , Jian Yu . Facile synthesis of high-brightness green-emitting carbon dots with narrow bandwidth towards backlight display. Chinese Chemical Letters, 2024, 35(5): 108763-. doi: 10.1016/j.cclet.2023.108763
20. [20]
  Genxiang Wang , Linfeng Fan , Peng Wang , Junfeng Wang , Fen Qiao , Zhenhai Wen . Efficient synthesis of nano high-entropy compounds for advanced oxygen evolution reaction. Chinese Chemical Letters, 2025, 36(4): 110498-. doi: 10.1016/j.cclet.2024.110498

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(527)
HTML views(0)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return