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

Base Information

Chemical Name:methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-galactopyranosid)uronate
CAS No.:311350-26-2
Molecular Formula:C₃₁H₃₆O₇S
Molecular Weight:552.689
Hs Code.:

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

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Chemical Property of methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-galactopyranosid)uronate

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Technology Process of methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-galactopyranosid)uronate

There total 7 articles about methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-galactopyranosid)uronate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 67-56-1
methanol

: (2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-ethylsulfanyl-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

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

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1080/07328300008544125

Reference yield:

: 56245-60-4,686299-00-3
ethyl 1-thio-β-D-galactopyranoside

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

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / p-TsOH*H₂O / dimethylformamide / 2 h / 40 °C / 30 Torr

2.1: NaH / dimethylformamide / 0.75 h / 0 °C

2.2: 82 percent / dimethylformamide

3.1: 92 percent / sodium cyanoborohydride; chlorotrimethylsilane / acetonitrile / 0 - 20 °C

4.1: DMSO; N,N'-dicyclohexylcarbodiimide; further reagents / 24 h / 20 °C

5.1: 906 mg / pyridinium dichromate / dimethylformamide / 24 h / 20 °C

With dipyridinium dichromate; chloro-trimethyl-silane; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: deprotonation / 2.2: Alkylation / 3.1: Ring cleavage / 4.1: Pfitzner-Moffat oxidation / 5.1: Oxidation;
DOI:10.1080/07328300008544125

Reference yield:

: 311797-19-0
ethyl 4,6-O-p-methoxybenzylidene-1-thio-β-D-galactopyranoside

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 0.75 h / 0 °C

1.2: 82 percent / dimethylformamide

2.1: 92 percent / sodium cyanoborohydride; chlorotrimethylsilane / acetonitrile / 0 - 20 °C

3.1: DMSO; N,N'-dicyclohexylcarbodiimide; further reagents / 24 h / 20 °C

4.1: 906 mg / pyridinium dichromate / dimethylformamide / 24 h / 20 °C

With dipyridinium dichromate; chloro-trimethyl-silane; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; acetonitrile; 1.1: deprotonation / 1.2: Alkylation / 2.1: Ring cleavage / 3.1: Pfitzner-Moffat oxidation / 4.1: Oxidation;
DOI:10.1080/07328300008544125