D-mannitol 1,6-di-(tert-butyldimethylsilyl)-2:4,3:5-O²:O⁴,O³:O⁵-bis(phenylboronate) | 666704-18-3

• 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: D-mannitol 1,6-di-(tert-butyldimethylsilyl)-2:4,3:5-O²:O⁴,O³:O⁵-bis(phenylboronate)
• 英文别名: [(4R,4aR,8R,8aR)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3,2]dioxaborinino[5,4-d][1,3,2]dioxaborinin-8-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 666704-18-3
• 化学式: C₃₀H₄₈B₂O₆Si₂
• 分子量: 582.501
• InChiKey: CABASWZKJFGURW-BIYDSLDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-mannitol 1,6-di-(tert-butyldimethylsilyl)-2:4,3:5-O²:O⁴,O³:O⁵-bis(phenylboronate) 在 双氧水 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 4.0h， 以62%的产率得到D-mannitol 1,6-di-(tert-butyldimethylsilyl) 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
• 作为产物：
  描述：

  甘露醇 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 50.0h， 生成 D-mannitol 1,6-di-(tert-butyldimethylsilyl)-2:4,3:5-O²:O⁴,O³:O⁵-bis(phenylboronate)
  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

• 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.