benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->2)-O-<(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)>-3-O-benzyl-α-D-glucopyranoside | 83236-93-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->2)-O-<(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)>-3-O-benzyl-α-D-glucopyranoside
• 英文别名: benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->2)-O-[(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)]-3-O-benzyl-α-D-glucopyranoside；(2R,3R,4S,5R,6S)-4,6-bis(phenylmethoxy)-5-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-[[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxan-3-ol
• CAS: 83236-93-5
• 化学式: C₈₈H₉₂O₁₆
• 分子量: 1405.69
• InChiKey: XJLZKDUTHAUUIZ-SRAKRBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.67
• 重原子数：
  104.0
• 可旋转键数：
  37.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  158.68
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->2)-O-<(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)>-3-O-benzyl-α-D-glucopyranoside 生成 [(2R,3R,4R,5R,6S)-4,6-bis(phenylmethoxy)-5-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-[[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl] 4-nitrobenzenesulfonate
  参考文献：
  名称：

  KOTO, SHINKITI;MORISHIMA, NAOHIKO;UCHINO, MASAHARU;FUKUDA, MISA;YAMAZAKI,+, BULL. CHEM. SOC. JAP., 61,(1988) N1, C. 3943-3950

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->2)-O-<(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)>-4-O-allyl-3-O-benzyl-α-D-glucopyranoside 以81%的产率得到benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->2)-O-<(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)>-3-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  SYNTHESIS OF A TRIFURCATED TETRASACCHARIDE USING DEHYDRATIVE GLYCOSYLATION

  摘要：

  2,6-二-O-(β-d-吡喃葡萄糖基)-4-O-(α-l-吡喃鼠李糖基)-d-吡喃葡萄糖是通过从糖基受体苄基开始的三个连续糖基化合成的，其中苄基保护的糖基4-O-烯丙基-6-O-苯甲酰基-3-O-苄基-α-d-吡喃葡萄糖苷。

  DOI：

  10.1246/cl.1982.1183

文献信息

• Synthesis of Branched-Chain Oligosaccharides in Sarsasaponins by Dehydrative Glycosylation
  作者：Shinkiti Koto、Naohiko Morishima、Masaharu Uchino、Misa Fukuda、Masayo Yamazaki、Shonosuke Zen

  DOI：10.1246/bcsj.61.3943

  日期：1988.11

  The branched-chain oligosaccharides, 6-O-(β-d-glucopyranosyl)-4-O-(α-l-rhamnopyranosyl)-d-glucopyranose, and 2,6-di-O-β-d-glucopyranosyl)-4-O-(α-l-rhamnopyranosyl)-d-glucopyranose, which compose sarsasaponins, as well as the structurally related 2-O-(β-d-glucopyranosyl)-4-O-(α-l-rhamnopyranosyl)-d-glucopyranose were synthesized stepwise via dehydrative glycosylation by a ternary mixture of p-nitrobenzenesulfonyl chloride, silver triflate, and triethylamine.

  组成沙棘皂苷的支链低聚糖、6-O-(β-d-吡喃葡萄糖基)-4-O-(α-l-吡喃鼠李糖基)-d-吡喃葡萄糖和2,6-二-O-β-d-吡喃葡萄糖基)-4-O-(α-l-吡喃鼠李糖基)-d-吡喃葡萄糖，以及结构相似的2-O-(β-d-吡喃葡萄糖基)-4-O-(α-l-吡喃鼠李糖基)-d-吡喃葡萄糖，是通过对硝基苯磺酰氯、三氟甲基磺酸银和三乙胺的三元混合物进行脱水糖基化逐步合成的。