D-mannitol 1,6-di-(tert-butyldiphenylsilyl) ether | 666704-24-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: D-mannitol 1,6-di-(tert-butyldiphenylsilyl) ether
• 英文别名: 1,6-di-O-tert-butyldiphenylsilyl-D-mannitol；(2R,3R,4R,5R)-1,6-bis[[tert-butyl(diphenyl)silyl]oxy]hexane-2,3,4,5-tetrol
• CAS: 666704-24-1
• 化学式: C₃₈H₅₀O₆Si₂
• 分子量: 658.982
• InChiKey: PQIOZDUCJMTDDD-MGXDLYCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-mannitol 1,6-di-(tert-butyldiphenylsilyl) ether 在 lead(IV) acetate 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (tert-butyldiphenylsilanyloxy)acetaldehyde
  参考文献：
  名称：

  修饰的核苷。N，O- psiconucleosides的一般和非对映选择性方法

  摘要：

  向新的类的一种有效的反应路线Ñ，ö -psiconucleosides已被设计，基于所述1,3-偶极环加成Ç - [（叔-butyldiphenylsilyl）氧基]甲基ñ -甲基硝酮与2- acetyloxyacrylate，然后进行核苷化。该方法已成功应用于所有嘧啶和嘌呤核苷碱基。

  DOI：

  10.1016/s0040-4020(01)01161-9
• 作为产物：
  描述：

  甘露醇 在 咪唑 、 双氧水 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 6.0h， 生成 D-mannitol 1,6-di-(tert-butyldiphenylsilyl) ether
  参考文献：
  名称：

  The Selective Silylation of d‐Mannitol Assisted by Phenylboronic Acid and the Solid State and Solution Structures of the Intermediate 1,6‐bis(silyl) bis(phenylboronates)

  摘要：

  The influence of phenylboronic acid on the silylation of D-mannitol by TBDMSCI and TBDPSCI has been investigated. Terminal silyation was found to dominate, with PBA significantly enhancing the yield of 1,6 di-TBDMS D-mannitol compared to the control. The intermediate 1,6-disilyl bis(phenylboronates) showed unusually high stability, such that oxidative conditions were required to cleave the boronate esters. X-ray crystal structures of both bis(phenylboronates) were determined, revealing both diboronate esters to exist as two fused six-membered rings. The results of B-11 NMR experiments suggest that these structures also predominate in solution, whereas the bis(phenylboronate) ester of D-mannitol itself exists as a mixture of five-membered and six-membered cyclic boronates.

  DOI：

  10.1081/car-120026598

文献信息

• [EN] SUGAR ALCOHOL-BASED CROSSLINKING REAGENTS, MACROMOLECULES, THERAPEUTIC BIOCONJUGATES, AND SYNTHETIC METHODS THEREOF<br/>[FR] NOUVEAUX RÉACTIFS DE RÉTICULATION, NOUVELLES MACROMOLÉCULES, NOUVEAUX CONJUGUÉS THÉRAPEUTIQUES, ET PROCÉDÉS DE SYNTHÈSE ASSOCIÉS
  申请人：CELLMOSAIC LLC

  公开号：WO2013012961A3

  公开（公告）日：2013-08-01
• Modified nucleosides. A general and diastereoselective approach to N,O-psiconucleosides
  作者：Daniela Iannazzo、Anna Piperno、Venerando Pistarà、Antonio Rescifina、Roberto Romeo

  DOI：10.1016/s0040-4020(01)01161-9

  日期：2002.1

  An efficient reaction route towards the new class of N,O-psiconucleosides has been designed, based on the 1,3-dipolar cycloaddition of C-[(tert-butyldiphenylsilyl)oxy]methyl-N-methyl nitrone with ethyl 2-acetyloxyacrylate, followed by nucleosidation. The process has been successfully applied to all pyrimidine and purine nucleobases.

  向新的类的一种有效的反应路线Ñ，ö -psiconucleosides已被设计，基于所述1,3-偶极环加成Ç - [（叔-butyldiphenylsilyl）氧基]甲基ñ -甲基硝酮与2- acetyloxyacrylate，然后进行核苷化。该方法已成功应用于所有嘧啶和嘌呤核苷碱基。
• The Selective Silylation of <scp>d</scp>‐Mannitol Assisted by Phenylboronic Acid and the Solid State and Solution Structures of the Intermediate 1,6‐bis(silyl) bis(phenylboronates)
  作者：Vijaya Bhaskar、Angelo D'Elia、Peter J. Duggan、David G. Humphrey、Guy Y. Krippner、Trang T. Nhan、Edward M. Tyndall

  DOI：10.1081/car-120026598

  日期：2003.12.31

  The influence of phenylboronic acid on the silylation of D-mannitol by TBDMSCI and TBDPSCI has been investigated. Terminal silyation was found to dominate, with PBA significantly enhancing the yield of 1,6 di-TBDMS D-mannitol compared to the control. The intermediate 1,6-disilyl bis(phenylboronates) showed unusually high stability, such that oxidative conditions were required to cleave the boronate esters. X-ray crystal structures of both bis(phenylboronates) were determined, revealing both diboronate esters to exist as two fused six-membered rings. The results of B-11 NMR experiments suggest that these structures also predominate in solution, whereas the bis(phenylboronate) ester of D-mannitol itself exists as a mixture of five-membered and six-membered cyclic boronates.