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

Base Information

• Chemical Name: methyl (ethyl 2,3-di-O-benzyl-4-O-methyl-1-thio-β-D-glucopyranoside)uronate
• CAS No.: 346435-08-3
• Molecular Formula: C₂₄H₃₀O₆S
• Molecular Weight: 446.565

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

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

Chemical Property:

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

There total 9 articles about methyl (ethyl 2,3-di-O-benzyl-4-O-methyl-1-thio-β-D-glucopyranoside)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: 92.0%

ethyl 2,3-di-O-benzyl-4-O-methyl-1-thio-β-D-glucopyranosiduronic acid + diazomethyl-trimethyl-silane (18107-18-1) → methyl (ethyl 2,3-di-O-benzyl-4-O-methyl-1-thio-β-D-glucopyranoside)uronate (346435-08-3)

Guidance literature:

In methanol; hexane; toluene; for 3h;

DOI:10.1002/ejoc.202000211

Reference yield:

methanol (67-56-1) + (2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-ethylsulfanyl-3-methoxy-tetrahydro-pyran-2-carbaldehyde → methyl (ethyl 2,3-di-O-benzyl-4-O-methyl-1-thio-β-D-glucopyranoside)uronate (346435-08-3)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1039/b009670a

Reference yield:

ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside (152964-70-0) → methyl (ethyl 2,3-di-O-benzyl-4-O-methyl-1-thio-β-D-glucopyranoside)uronate (346435-08-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / pyridine / 55 °C

2.1: NaH / light petroleum; dimethylformamide / 1 h / 0 °C

2.2: light petroleum; dimethylformamide / 3 h / 0 - 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

4.1: 934 mg / PDC / dimethylformamide / 20 °C

With pyridine; dipyridinium dichromate; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; Petroleum ether; 3.1: Swern oxidation;

DOI:10.1039/b009670a

upstream raw materials:

methanol

ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

Ethyl 2,3-di-O-benzyl-6-O-triphenylmethyl-1-thio-β-D-glucopyranoside

ethyl 1-thio-β-D-glucopyranoside

Downstream raw materials:

p-Methoxyphenyl (methyl 2,3-di-O-benzyl-4-O-methyl-α-D-glucopyranosyluronate)-(1->2)-[3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-xylopyranosyl]-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside

p-Methoxyphenyl (methyl 2,3-di-O-acetyl-4-O-methyl-α-D-glucopyranosyluronate)-(1->2)-(3,4-O-di-acetyl-β-D-xylopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside

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