(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran | 118545-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran
• 英文别名: tert-butyl-[[(2R,3R,4R,5R,6S)-3-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methoxy]-dimethylsilane
• CAS: 118545-10-1
• 化学式: C₃₃H₅₄O₆Si₂
• 分子量: 602.959
• InChiKey: ROJRRCFGJRPEGC-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 以95%的产率得到Bn(-2)[Bn(-3)][TBDMS(-4)]a-Glc1Me
  参考文献：
  名称：

  Cross-metathesis and ring-closing metathesis of olefinic monosaccharides

  摘要：

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01617-9
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 2,3-二-o-苄基-alpha-d-吡喃葡萄糖苷甲酯 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到(2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran
  参考文献：
  名称：

  一种高效合成六吡喃糖苷丙酮酸缩醛的新方法

  摘要：

  乙缩醛制备了二-O-苄基-2,3 O-甲基-1六吡喃糖苷（甘露糖，葡萄糖等）的部分和丙酮基丙酮酸或苄基丙烯酰胺的甲硅烷基化反应

  DOI：

  10.1016/0008-6215(88)85070-5

文献信息

• A two directional glycosylation strategy for the convergent assembly of oligosaccharides
  作者：Tong Zhu、Geert-Jan Boons

  DOI：10.1016/s0040-4039(98)00171-3

  日期：1998.4

  A novel glycosylation strategy has been developed whereby a silyl protected thioglycoside can act as both glycosyl donor and acceptor. Taking advantage of a two directional approach in combination with previously reported orthogonal glycosylations, enables highly convergent and versatile assembly of oligosaccharides.

  已经开发了一种新颖的糖基化策略，其中甲硅烷基保护的硫代糖苷可以同时充当糖基供体和受体。利用双向方法与先前报道的正交糖基化相结合，可实现寡糖的高度收敛和通用组装。
• Convenient synthesis of pyruvate acetals of carbohydrates by coupling of trialkylsilylated diols and pyruvates
  作者：Kazumi Hiruma、Jun-ichi Tamura、Sigeomi Horito、Juji Yoshimura、Hironobu Hashimoto

  DOI：10.1016/s0040-4020(01)89567-3

  日期：1994.1

  Hexopyranoside diols, mainly 4,6-diols with alpha-gluco, beta-gluco, alpha-galacto, beta-galacto, and alpha-manno configurations could be converted effectively (40 - 74% yields), to the corresponding pyruvate acetals by the coupling of the O-trialkylsilylated, namely, O-TBDMS and/or O-TMS diols, and ethyl pyruvate in the presence of TMSOTf at temperatures between -30 degrees C and +3 degrees C. In the case of the beta-manno isomer, the anomerization of the beta-glycoside to the alpha-glycoside as well as the ring contraction of the pyranoside to the furanoside predominated.
• HASHIMOTO, HIRONOBU;HIRUMA, KAZUMI;TAMURA, JUN-ICHI, CARBOHYDR. RES., 177,(1988) C9-C12
  作者：HASHIMOTO, HIRONOBU、HIRUMA, KAZUMI、TAMURA, JUN-ICHI

  DOI：——

  日期：——