methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-galactopyranosid)uronate | 311350-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-galactopyranosid)uronate
• 英文别名: methyl (2S,3R,4S,5R,6S)-6-ethylsulfanyl-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxane-2-carboxylate
• CAS: 311350-26-2
• 化学式: C₃₁H₃₆O₇S
• 分子量: 552.689
• InChiKey: MDXJRXDBRZBBMB-HRTQWJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-galactopyranosid)uronate 在 iodonium(di-γ-collidine) perchlorate 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 18.67h， 生成 methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-galactopyranosyluronate)-(1->4)-(methyl 2,3-di-O-benzyl-α-D-galactopyranosyluronate)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of Homogalacturonan Fragments

  摘要：

  Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides alpha(1-->4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the alpha(1 "-->4')-linked trimer 39 (48%). Approximately 8% of the beta(1 "-->4')-coupled isomer was observed in the C-13 NMR spectrum of the reaction mixture.

  DOI：

  10.1080/07328300008544125
• 作为产物：
  描述：

  1-硫代-Β-D-乙基半乳糖苷 在 重铬酸吡啶 、 三甲基氯硅烷 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 40.0 ℃ 、4.0 kPa 条件下， 反应 50.75h， 生成 methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of Homogalacturonan Fragments

  摘要：

  Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides alpha(1-->4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the alpha(1 "-->4')-linked trimer 39 (48%). Approximately 8% of the beta(1 "-->4')-coupled isomer was observed in the C-13 NMR spectrum of the reaction mixture.

  DOI：

  10.1080/07328300008544125

文献信息

• Synthesis of Rhamnogalacturonan I Fragments
  作者：Birte Nolting、Hanna Boye、Christian Vogel

  DOI：10.1080/07328300008544126

  日期：2000.1

  The partially deprotected trisaccharide 17 has been synthesized as an analogue of the repeating unit of the backbone of rhamnogalacturonan I. The trisaccharide 17 was obtained after prior selective derivatization of HO-3 and HO-4 of a rhamnopyranose cyanoethylidene glycosyl donor, followed by coupling with a tritylated galactopyranosyluronic acceptor (11), selective removal of the acetyl group at the O-2' position of the formed disaccharide 12, and glycosylation of the HO-2' position with methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-beta-D-galactopyranosid)uronate (14) providing methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-alpha-D-galactopyranosyluronate)-(1-->2)-(4-O-benzoyl-3-O-benzyl-alpha-L-rhamnopyranosyl)-(1-->4)-(allyl 2,3-di-O-benzyl-beta-D-galactopyranosid)uronate (15). Finally, palladium chloride catalyzed deallylation (16) and hydrogenolysis over Pd-C resulted in methyl (methyl alpha-D-galactopyranosyluronate)(1-->2)-(4-O-benzoyl-alpha-L-rhamnopyranosyl)-(1-->4)-alpha/beta D-galactopyranuronate (17).
• Synthesis of Homogalacturonan Fragments
  作者：Sven Kramer、Birte Nolting、Andrej-Jakob Ott、Christian Vogel

  DOI：10.1080/07328300008544125

  日期：2000.1

  Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides alpha(1-->4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the alpha(1 "-->4')-linked trimer 39 (48%). Approximately 8% of the beta(1 "-->4')-coupled isomer was observed in the C-13 NMR spectrum of the reaction mixture.