methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside | 21317-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside
• 英文别名: methyl α-D-amicetoside；(2R,3S,6S)-6-methoxy-2-methyloxan-3-ol
• CAS: 21317-50-0
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: CWBJMXOKTZGNEH-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside 在 吡啶 、 溶剂黄146 作用下， 反应 2.0h， 生成 4-O-benzylsulfonyl-2,3,6-trideoxy-β-D-erythro-hexopyranose
  参考文献：
  名称：

  β-连接的2,6-脱氧寡糖的直接和立体选择性合成。

  摘要：

  DOI：

  10.1002/anie.200604031
• 作为产物：
  描述：

  methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-erythrohexopyranoside 在 sodium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 20.25h， 生成 methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside
  参考文献：
  名称：

  Synthesis of the polyketomycin disaccharide

  摘要：

  The disaccharide portion of the anthracycline antibiotic polyketomycin consists of the trideoxy sugar D-amicetose attached to the methyl-branched sugar L-axenose. The polyketomycin disaccharide was synthesized from methyl 2,3,6-trideoxy-alpha-D-erythro-hexopyranoside (methyl alpha-D-amicetoside) and phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-l-thio-alpha,beta-L-xylo-hexopyranoside. The key coupling step was carried out by N-bromosuccinimide activation of the thioglycoside and gave the desired alpha (1-->4) linked disaccharide exclusively in 71% yield, which was debenzylated by sodium and liquid ammonia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.023

文献信息

• Synthesis of some trideoxy- d -hexoses and derivatives thereof from d -glucono-1,5-lactone
  作者：Henk Regeling、Gordon J. F. Chittenden

  DOI：10.1016/0008-6215(92)84152-i

  日期：1992.9

  methyl 2,3,4-trideoxy-α- d - and -β- d -glycero-hexopyranoside (10 and 11) methyl α- d - and β- d -amicetopyranoside (24 and 25), (2S)-1,2-hexanediol (36), (2S)-1,2,6-hexanetriol (37), and some derivatives thereof from d -glucono-1,5-lactone are described.

  摘要甲基2,3,4-丁氧基-α-d-和-β-d-甘油己吡喃糖苷（10和11）甲基α-d-和β-d-乙酰吡喃糖苷（24和25），（2S描述了）-1,2-己二醇（36），（2S）-1,1,2,6-己三醇（37），以及它们的一些衍生自d-葡萄糖基-1,5-内酯的衍生物。
• Thioanhydro sugars. Part IX: Enantiospecific synthesis of a polyhydroxythio lane, key intermediate for the preparation of glycosidase inhibitors bearing inner thiosulfonium salt
  作者：Isidoro Izquierdo、Marı́a T. Plaza、Rafael Asenjo、Antonio Ramı́rez

  DOI：10.1016/s0957-4166(02)00368-3

  日期：2002.7

  (2R,3R,4S)-3,4-Dihydroxy-2-[(R)-1,2-dihydroxyethyl]thiolane (1,4-anhydro-4-thio-D-mannitol), 1 has been prepared from methyl 4,6-O-benzylidene-alpha-D-altropyranoside 2 in seven steps, the latter being readily available from commercial methyl alpha-D-glucopyranoside. (C) 2002 Elsevier Science Ltd. All rights reserved.

  (2R,3R,4S)-3,4-二羟基-2-[(R)-1,2-二羟基乙基]硫杂环己烷（1,4-无水-4-硫-D-甘露醇），1，已由甲基4,6-O-苯甲酰-α-D-阿罗吡喃糖苷2经七步制得，后者由市售的甲基α-D-葡萄吡喃糖苷方便得到。
• Polyketomycin, a New Antibiotic from Streptomyces sp. MK277-AF1. II. Structure Determination.
  作者：ISAO MOMOSE、WEI CHEN、HIKARU NAKAMURA、HIROSHI NAGANAWA、HIRONOBU IINUMA、TOMIO TAKEUCHI

  DOI：10.7164/antibiotics.51.26

  日期：——

  A new antibiotic, polyketomycin, was isolated from the culture broth of Streptomyces sp. MK277-AF1. The structure was determined by various NMR spectroscopies, X-ray crystallographic analysis and degradation experiments.

  从链霉菌属（Streptomyces sp。）的培养液中分离出新的抗生素聚酮霉素。MK277-AF1。通过各种NMR光谱，X射线晶体学分析和降解实验确定结构。
• Kjoelberg, Ove; Neumann, Klaus, Acta Chemica Scandinavica, 1992, vol. 46, # 9, p. 877 - 882
  作者：Kjoelberg, Ove、Neumann, Klaus

  DOI：——

  日期：——
• Synthesis of methyl 2,6-dideoxy-4-thio-α-D-ribo-hexopyranoside, a new thio sugar found in calichemicins
  作者：Kai Van Laak、Hans-Dieter Scharf

  DOI：10.1016/s0040-4039(01)80729-2

  日期：1989.1