phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-D-glycero-α-D-thio-manno-heptopyranoside

Base Information

Chemical Name:phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-D-glycero-α-D-thio-manno-heptopyranoside
CAS No.:902751-06-8
Molecular Formula:C₃₅H₃₆O₇S
Molecular Weight:600.733
Hs Code.:

Synonyms:phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-D-glycero-α-D-thio-manno-heptopyranoside

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Chemical Property of phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-D-glycero-α-D-thio-manno-heptopyranoside

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Technology Process of phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-D-glycero-α-D-thio-manno-heptopyranoside

There total 4 articles about phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-D-glycero-α-D-thio-manno-heptopyranoside 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: 87.0%

: 850647-89-1
phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-D-glycero-α-D-thio-manno-heptopyranoside

: 902751-06-8
phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-D-glycero-α-D-thio-manno-heptopyranoside

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 1h;
DOI:10.1021/ja061594u

Reference yield:

: 850647-86-8
phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside

: 902751-06-8
phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-D-glycero-α-D-thio-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -50 °C

1.2: 65 percent / nBuLi / tetrahydrofuran; hexane / 1 h / -40 °C

2.1: 61 percent / NMNO; OsO₄ / 2-methyl-propan-2-ol / 4 h / 20 °C

3.1: 87 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

With osmium(VIII) oxide; oxalyl dichloride; bis-(2-chloro-ethyl)-methyl-amine oxide; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ja061594u

Reference yield:

: 850647-87-9
phenyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-α-D-thiohept-6-enopyranoside

: 902751-06-8
phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-D-glycero-α-D-thio-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 61 percent / NMNO; OsO₄ / 2-methyl-propan-2-ol / 4 h / 20 °C

2: 87 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

With osmium(VIII) oxide; bis-(2-chloro-ethyl)-methyl-amine oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ja061594u