2,3,4,6-Tetra-O-benzyl-1-C-(dichloromethyl)-D-glucitol | 116308-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-Tetra-O-benzyl-1-C-(dichloromethyl)-D-glucitol
• 英文别名: (3S,4S,5R,6R)-1,1-dichloro-3,4,5,7-tetrakis(phenylmethoxy)heptane-2,6-diol
• CAS: 116308-14-6；116348-71-1
• 化学式: C₃₅H₃₈Cl₂O₆
• 分子量: 625.589
• InChiKey: OWOCPGYQPYDORM-VBQYTDQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-Tetra-O-benzyl-1-C-(dichloromethyl)-D-glucitol 在 甲酸 、 偶氮二异丁腈 、 三正丁基氢锡 、 钯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 7.0h， 生成 1-Deoxy-D-glycero-D-gulo-heptitol
  参考文献：
  名称：

  Synthesis of a branched-chain inosose derivative, a versatile synthon of N-substituted valiolamine derivatives from D-glucose

  摘要：

  The synthesis of (1S)-(1(OH)-2,4/1,3)-2,3,4-tri-O-benzyl-1-C-[(benzyloxy)methyl]-5-oxo-1,2,3,4-cyclohexanetetrol (7), which is an important synthon for the synthesis of valiolamine (8) 2 and its N-substituted derivatives such as AO-128 (9)3 having strong alpha-D-glucosidase inhibitory activity, is described. This branched-chain inosose derivative 7 has been prepared from the D-glucono-1,5-lactone derivative 2 which is readily available from D-glucose (1). The key step in the synthesis involves the stereospecific intramolecular carbocyclic ring, closure of the 1-deoxy-2, 6-heptodiulose derivatives 5a and 5b obtained by the oxidation of 2,3,4,6-tetra-O-benzyl-1-C-[bis-(methylthio)methyl]-D-glucitol (4a) and 2,3,4,6-tetra-O-benzyl-1-C-(dichloromethyl)-D-glucitol (4b). The resulting branched-chain bis(methylthio)inosose derivative 6a and dichloroinosose derivative 6b have been converted to the desired branched-chain inosose derivative 7 by desulfurization of 6a and dechlorination of 6b.

  DOI：

  10.1021/jo00039a025
• 作为产物：
  描述：

  toluene-ethyl acetate 、 2,3,4,6-tetra-O-benzyl-1-C-(dichloromethyl)-D-glucopyranose 在 sodium borohydrid 作用下， 以 四氢呋喃 为溶剂， 生成 2,3,4,6-Tetra-O-benzyl-1-C-(dichloromethyl)-D-glucitol
  参考文献：
  名称：

  Inosose derivatives, production and use thereof

  摘要：

  本发明揭示了一种新型的inosose化合物，其通式表示为：##STR1## 其中X.sup.1和X.sup.2均为卤素；X.sup.1为氢，X.sup.2为卤素；或者X.sup.1为--SQ.sup.1，X.sup.2为--SQ.sup.2（其中Q.sup.1和Q.sup.2各自为较低的烷基或Q.sup.1和Q.sup.2可形成较低的烷基烯），R.sup.1为羟基的保护基，Y为.dbd.O，.dbd.N--Z（Z为可能被保护的羟基）或者##STR2##（A为氢或胺基残基），特别是其中符号Y为氧的化合物。这种inosose化合物可用作制备valiolamine及其N-取代衍生物的中间体，这些衍生物具有强大的α-葡萄糖苷酶抑制活性，可用作预防或治疗人类和动物的高血糖症状及由此引起的各种疾病，如糖尿病、肥胖症和高脂血症。

  公开号：

  US04898986A1

文献信息

• US4898986A
  申请人：——

  公开号：US4898986A

  公开（公告）日：1990-02-06
• US5004838A
  申请人：——

  公开号：US5004838A

  公开（公告）日：1991-04-02
• Synthesis of a branched-chain inosose derivative, a versatile synthon of N-substituted valiolamine derivatives from D-glucose
  作者：Hiroshi Fukase、Satoshi Horii

  DOI：10.1021/jo00039a025

  日期：1992.6

  The synthesis of (1S)-(1(OH)-2,4/1,3)-2,3,4-tri-O-benzyl-1-C-[(benzyloxy)methyl]-5-oxo-1,2,3,4-cyclohexanetetrol (7), which is an important synthon for the synthesis of valiolamine (8) 2 and its N-substituted derivatives such as AO-128 (9)3 having strong alpha-D-glucosidase inhibitory activity, is described. This branched-chain inosose derivative 7 has been prepared from the D-glucono-1,5-lactone derivative 2 which is readily available from D-glucose (1). The key step in the synthesis involves the stereospecific intramolecular carbocyclic ring, closure of the 1-deoxy-2, 6-heptodiulose derivatives 5a and 5b obtained by the oxidation of 2,3,4,6-tetra-O-benzyl-1-C-[bis-(methylthio)methyl]-D-glucitol (4a) and 2,3,4,6-tetra-O-benzyl-1-C-(dichloromethyl)-D-glucitol (4b). The resulting branched-chain bis(methylthio)inosose derivative 6a and dichloroinosose derivative 6b have been converted to the desired branched-chain inosose derivative 7 by desulfurization of 6a and dechlorination of 6b.
• Inosose derivatives, production and use thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04898986A1

  公开（公告）日：1990-02-06

  Disclosed is a novel inosose compound represented by the general formula: ##STR1## wherein X.sup.1 and X.sup.2 are both halogen; X.sup.1 is hydrogen and X.sup.2 is halogen; or X.sup.1 is --SQ.sup.1 and X.sup.2 is --SQ.sup.2 (each of Q.sup.1 and Q.sup.2 is lower alkyl or Q.sup.1 and Q.sup.2 may form lower alkylene), R.sup.1 is a protective group for hydroxyl and Y is .dbd.O, .dbd.N--Z (Z is hydroxyl which may be protected) or ##STR2## (A is hydrogen or an amine residue), particularly to the compound wherein the symbol Y is oxygen. The inosose compound is useful as intermediates for production of valiolamine and the N-substituted derivatives thereof, which have potent .alpha.-glucosidase inhibiting activities and are useful as preventives or therapeutics for symptoms of hyperglycemia and various diseases derived therefrom in human and animals, such as diabetes, obesity and hyperlipemia.

  本发明揭示了一种新型的inosose化合物，其通式表示为：##STR1## 其中X.sup.1和X.sup.2均为卤素；X.sup.1为氢，X.sup.2为卤素；或者X.sup.1为--SQ.sup.1，X.sup.2为--SQ.sup.2（其中Q.sup.1和Q.sup.2各自为较低的烷基或Q.sup.1和Q.sup.2可形成较低的烷基烯），R.sup.1为羟基的保护基，Y为.dbd.O，.dbd.N--Z（Z为可能被保护的羟基）或者##STR2##（A为氢或胺基残基），特别是其中符号Y为氧的化合物。这种inosose化合物可用作制备valiolamine及其N-取代衍生物的中间体，这些衍生物具有强大的α-葡萄糖苷酶抑制活性，可用作预防或治疗人类和动物的高血糖症状及由此引起的各种疾病，如糖尿病、肥胖症和高脂血症。