octyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-1-thioglucopyranoside | 1194234-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-1-thioglucopyranoside
• 英文别名: octyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-thioglucopyranoside
• CAS: 1194234-32-6
• 化学式: C₃₅H₄₄O₅S
• 分子量: 576.797
• InChiKey: BZMPJHYRCIQJQE-RFQHCYMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  41.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  octyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-1-thioglucopyranoside 在 盐酸 、 lithium aluminium tetrahydride 、 四丁基溴化铵 、 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 2-hexyl-1-octyl 6-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates

  摘要：

  Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation Of octyl beta-D-glucopyranoside with acid anhydrides derived from alpha-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R' = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by I was found to be high.

  DOI：

  10.1021/jo901569v
• 作为产物：
  描述：

  辛基-beta-D-硫代吡喃葡萄糖苷 在 D(+)-10-樟脑磺酸 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 2.0h， 生成 octyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-1-thioglucopyranoside
  参考文献：
  名称：

  Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates

  摘要：

  Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation Of octyl beta-D-glucopyranoside with acid anhydrides derived from alpha-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R' = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by I was found to be high.

  DOI：

  10.1021/jo901569v

文献信息

• A Visible-Light-Promoted <i>O</i> -Glycosylation with a Thioglycoside Donor
  作者：Mark L. Spell、Kristina Deveaux、Caitlin G. Bresnahan、Bradley L. Bernard、William Sheffield、Revati Kumar、Justin R. Ragains

  DOI：10.1002/anie.201601566

  日期：2016.5.23

  Visible‐light irradiation of 4‐p‐methoxyphenyl‐3‐butenylthioglucoside donors in the presence of Umemoto's reagent and alcohol acceptors serves as a mild approach to O‐glycosylation. Visible‐light photocatalysts are not required for activation, and alkyl‐ and arylthioglycosides not bearing the p‐methoxystyrene are inert to these conditions. Experimental and computational evidence for an intervening

  在梅本试剂和醇受体存在下，对4-对-甲氧基苯基-3-丁烯基硫代葡萄糖苷供体的可见光照射是温和的O-糖基化方法。活化不需要可见光光催化剂，不带有对甲氧基苯乙烯的烷基和芳基硫代糖苷对这些条件呈惰性。提供了反应性必需的中间电子供体-受体复合物的实验和计算证据。伯，仲和叔醇受体的产量范围从中等到高。完全的β-选择性可以通过邻群的参与来实现。