1,4-anhydro-5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-D-ribitol | 132617-86-8

• 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: 1,4-anhydro-5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-D-ribitol
• 英文别名: (3S)-1,4-anhydro-5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-D-ribitol；1,3-dideoxy-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-D-ribofuranose；[3R-(3α,4α,5β)]-tetrahydro-4,5-bis [(phenylmethoxy)methyl]-3-furanol；1,3-Dideoxy-3-[(phenylmethoxy)methyl]-5-O-(phenylmethyl)-D-ribofuranose；(3R,4S,5S)-4,5-bis(phenylmethoxymethyl)oxolan-3-ol
• CAS: 132617-86-8
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: HCKBKOSHUWANPE-SLFFLAALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-D-ribitol 在 Lindlar's catalyst 4-二甲氨基吡啶 、 叠氮化锂 、 硫酸 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.0h， 生成 <3S-(3α,4β,5α)>-1--3-furanyl>-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Nucleosides and nucleotides. 132. Synthesis and biological evaluations of ring-expanded oxetanocin analogues: Purine and pyrimidine analogues of 1,4-anhydro-2-deoxy-d-arabitol and 1,4-anhydro-2-deoxy-3-hydroxymethyl-d-arabitol

  摘要：

  (2R)-2-C-(Adenin-9-yl)-1,4-anhydro-2-deoxy-D-arabitol (2) 以及 (2R, 3R)-2-C-(adenin-9-yl)-1,4-anhydro-2,3-dideoxy-3-C-hydroxymethyl-D-arabitol (3) 与其对应的 2,6-diaminopurine 类似物 4 和 5，均通过相应 1,4-anhydro-D-ribitol 衍生物合成，这些衍生物可由 D-glucose 方便获得。通过腺苷脱氨酶催化去氨基反应，将化合物 4 和 5 转化为相应的鸟嘌呤异核苷 6 和 7。嘧啶类似物 8 和 9 则通过构建嘧啶基团，从 1,4-anhydro-D-arabitol 衍生物的氨基衍生物合成。在体外实验中，针对这些扩环的 oxetanocins 衍生物（包括 HSV-1、HSV-2、HCMV 和 HBV）的抗病毒活性进行了评估，同时测量了其对 L1210 和 KB 细胞的细胞毒性。

  DOI：

  10.1016/s0040-4020(01)81749-x
• 作为产物：
  描述：

  3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以84.5%的产率得到1,4-anhydro-5-O-benzyl-3-C-benzyloxymethyl-3-deoxy-D-ribitol
  参考文献：
  名称：

  Nucleosides and nucleotides. 132. Synthesis and biological evaluations of ring-expanded oxetanocin analogues: Purine and pyrimidine analogues of 1,4-anhydro-2-deoxy-d-arabitol and 1,4-anhydro-2-deoxy-3-hydroxymethyl-d-arabitol

  摘要：

  (2R)-2-C-(Adenin-9-yl)-1,4-anhydro-2-deoxy-D-arabitol (2) 以及 (2R, 3R)-2-C-(adenin-9-yl)-1,4-anhydro-2,3-dideoxy-3-C-hydroxymethyl-D-arabitol (3) 与其对应的 2,6-diaminopurine 类似物 4 和 5，均通过相应 1,4-anhydro-D-ribitol 衍生物合成，这些衍生物可由 D-glucose 方便获得。通过腺苷脱氨酶催化去氨基反应，将化合物 4 和 5 转化为相应的鸟嘌呤异核苷 6 和 7。嘧啶类似物 8 和 9 则通过构建嘧啶基团，从 1,4-anhydro-D-arabitol 衍生物的氨基衍生物合成。在体外实验中，针对这些扩环的 oxetanocins 衍生物（包括 HSV-1、HSV-2、HCMV 和 HBV）的抗病毒活性进行了评估，同时测量了其对 L1210 和 KB 细胞的细胞毒性。

  DOI：

  10.1016/s0040-4020(01)81749-x

文献信息

• Purinyl tetrahydrofurans
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05059690A1

  公开（公告）日：1991-10-22

  Antiviral activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1 is a purine or pyrimidine base or an analog thereof and R.sub.2 and R.sub.3 are independently hydrogen, --PO.sub.3 H.sub.2 or ##STR2## wherein X.sub.7 is hydrogen, alkyl, substituted alkyl or aryl.

  化合物具有以下结构式的抗病毒活性：##STR1##及其药学上可接受的盐，其中R.sub.1是嘌呤或嘧啶碱基或其类似物，R.sub.2和R.sub.3分别是氢、--PO.sub.3 H.sub.2或##STR2##其中X.sub.7是氢、烷基、取代烷基或芳基。
• Pyrimidinyl tetrahydrofurans
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05145960A1

  公开（公告）日：1992-09-08

  Antiviral activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1 is a pyrimidine base or an analog thereof and R.sub.2 and R.sub.3 are independently hydrogen, --PO.sub.3 H.sub.2 or ##STR2## wherein X.sub.7 is hydrogen, alkyl, substituted alkyl or aryl.

  具有以下式子的化合物及其药学上可接受的盐表现出抗病毒活性：##STR1##其中R.sub.1是嘧啶碱基或其类似物，R.sub.2和R.sub.3独立地是氢、--PO.sub.3 H.sub.2或##STR2##其中X.sub.7是氢、烷基、取代烷基或芳基。
• Purinyl and pyrimidinyl tetrahydrofurans
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0394893A2

  公开（公告）日：1990-10-31

  Antiviral activity is exhibited by compounds having the formula and pharmaceutically acceptable salts thereof wherein R1 is a purine or pyrimidine base or an analog thereof and R2 and R3 are independently hydrogen, -PO3H2 or - -X7, wherein X7 is hydrogen, alkyl, substituted alkyl or aryl.

  具有以下式子的化合物具有抗病毒活性 及其药学上可接受的盐类，其中 R1 是嘌呤或嘧啶碱或其类似物，R2 和 R3 独立地是氢、-PO3H2 或 -X7，其中 X7 是氢、烷基、取代的烷基或芳基。
• Process for preparing guanine-containing antiviral agents and purinyl salts useful in such process
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0579421A2

  公开（公告）日：1994-01-19

  A purine salt of the formula wherein Y₁ is chloro, bromo, or iodo, and R₁, R₂, R₃, and R₄ are independently selected from alkyl and substituted alkyl is reacted with the compound of the formula         Z₁―X to yield the purine of the formula wherein X is a leaving group, and Z₁ is a protected form of the carbohydrate surrogate Z. Several routes are disclosed for converting this intermediate to the antiviral agent

  式中的嘌呤盐 其中 Y₁ 是氯、溴或碘，且 R₁、R₂、R₃ 和 R₄ 独立选自烷基和取代烷基的嘌呤盐与式中的化合物反应 Z₁-X 与式 Z₁-X 的化合物反应，生成式 Z₁-X 的嘌呤 其中 X 是离去基团，Z₁ 是碳水化合物代用品 Z 的保护形式。
• Synthesis and antiviral activity of novel isonucleoside analogs
  作者：Joseph A. Tino、Junius M. Clark、A. Kirk Field、Glenn A. Jacobs、Karen A. Lis、Teresa L. Michalik、Bridgette McGeever-Rubin、William A. Slusarchyk、Steven H. Spergel

  DOI：10.1021/jm00061a013

  日期：1993.4

  A series of branched-chain sugar isonucleosides was synthesized and evaluated for antiviral activity against herpesviruses. The preparation of homochiral [3S-(3alpha,4beta,5alpha)]-2-amino-1,9-dihydro-9-[tetrahydro-4,5-bis(hydroxymethyl)-3-furanyl]-6H-purin-6-one (7, BMS-181,164) and related compounds was stereospecifically achieved starting from 1,2-isopropylidene-D-xylofuranose (10). An efficient two-step reduction of the anomeric center of bis-acetate 18 involved formation of the chloride intermediate 19, followed by diisobutylaluminum hydride reduction. Tosylation of the resulting alcohol 20 provided the key intermediate 21, which was coupled with a variety of nucleobase anions. Several members of this new class of compounds possess activity against herpes simplex virus types 1 and 2 (HSV-1 and -2), varicella-zoster virus (VZV), and human cytomegalovirus (HCMV). Compound 7 exhibits potent and selective activity against thymidine kinase encoding herpesviruses, in particular, HSV-1 and HSV-2. Evaluation of compound 7 for inhibition of WI-38 cell growth indicated an ID50 of > 700 muM. Although the antiherpetic activity in vitro of 7 is less than that of acyclovir (1), compound 7 displays superior efficacy in mouse model infections. The (bromovinyl)uridine analog 8 (BMS-181,165) also exhibits selective activity against HSV-1 and VZV, with no cytostatic effect on WI-38 cell growth at > 800 muM. Compound 8 is active against simian varicella virus and is efficacious in the corresponding monkey model.