methyl 2,3-di-O-benzyl-6-S-[(Z)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3-di-O-benzyl-6-S-[(Z)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside
CAS No.:894428-35-4
Molecular Formula:C₂₉H₃₂O₇S₂
Molecular Weight:556.701
Hs Code.:

Synonyms:methyl 2,3-di-O-benzyl-6-S-[(Z)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside

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Chemical Property of methyl 2,3-di-O-benzyl-6-S-[(Z)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside

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Technology Process of methyl 2,3-di-O-benzyl-6-S-[(Z)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside

There total 4 articles about methyl 2,3-di-O-benzyl-6-S-[(Z)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside 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: 91.0%

: 963-15-5
(Z)-1,2-bis(phenylsulfonyl)ethene

: 604757-18-8
methyl 2,3-di-O-benzyl-6-thio-α-D-glucopyranoside

: 894428-35-4
methyl 2,3-di-O-benzyl-6-S-[(Z)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside

Guidance literature:: With tetrabutylammomium bromide; triethylamine; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1016/j.tet.2006.03.023

Reference yield:

: 894428-34-3
methyl 2,3-di-O-benzyl-6-S-[(E)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside

: 894428-35-4
methyl 2,3-di-O-benzyl-6-S-[(Z)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 52 percent / NaH; Bu₄NBr / tetrahydrofuran / 12 h / 20 °C

2: 98 percent / LiAlH₄ / diethyl ether

3: 91 percent / Et₃N; Bu₄NBr / tetrahydrofuran / 12 h / 20 °C

With lithium aluminium tetrahydride; tetrabutylammomium bromide; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; 3: Michael addition;
DOI:10.1016/j.tet.2006.03.023

Reference yield:

: 17791-36-5
methyl 2,3-di-O-benzyl-α-D-glucopyranoside

: 894428-35-4
methyl 2,3-di-O-benzyl-6-S-[(Z)-2-(phenylsulfonyl)-vinyl]-6-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 68 percent / triphenylphosphine; diethyl azodicarboxylate / toluene / 20 °C

2: 90 percent / LiAlH₄ / diethyl ether / 4 h / Heating

3: 91 percent / Et₃N; Bu₄NBr / tetrahydrofuran / 12 h / 20 °C

With lithium aluminium tetrahydride; tetrabutylammomium bromide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; toluene; 1: Mitsunobu reaction / 3: Michael addition;
DOI:10.1016/j.tet.2006.03.023