Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside
• CAS No.: 151669-25-9
• Molecular Formula: C₂₂H₂₆O₇S₂
• Molecular Weight: 466.576

Synonyms:Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

Chemical Property of Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

Chemical Property:

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Technology Process of Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

There total 7 articles about Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside 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: 93.0%

p-toluenesulfonyl chloride (98-59-9) + phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside (126092-08-8) → Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside (151669-25-9)

Guidance literature:

With pyridine; at 0 - 25 ℃; for 12h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H

Reference yield: 89.0%

Phenyl 6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside (151669-24-8) + 2,2-dimethoxy-propane (77-76-9) → Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside (151669-25-9)

Guidance literature:

With toluene-4-sulfonic acid; for 0.5h;

DOI:10.1016/0008-6215(93)80060-R

Reference yield: 85.0%

toluene-4-sulfonic acid (104-15-4) + Phenyl 6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside (151669-24-8) + 2,2-dimethoxy-propane (77-76-9) → Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside (151669-25-9)

Guidance literature:

In water; N,N-dimethyl-formamide; for 7h; Inert atmosphere;

upstream raw materials:

Phenyl 6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

2,2-dimethoxy-propane

p-toluenesulfonyl chloride

phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

Toluene-4-sulfonic acid (3aS,4R,6R,7R,7aR)-2,2-dimethyl-4-phenylsulfanyl-7-triisopropylsilanyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

(2R,3S,4R,6S)-6-[(2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3,4-diol

(2R,3R,4R,6S)-4-Allyloxy-6-[(2R,3R,4S,5R)-4-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-ol

(2R,3R,4S,5R)-4-Benzyloxy-3-[(2S,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran

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