methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside
• CAS No.: 79297-68-0
• Molecular Formula: C₂₁H₂₄O₇S
• Molecular Weight: 420.483

Synonyms:methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside

Chemical Property:

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Technology Process of methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside

There total 10 articles about methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside 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: 68.0%

Imidazole-1-carbothioic acid O-[(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-(toluene-4-sulfonyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl] ester (79233-83-3) → methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside (79297-68-0)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1021/jo00337a004

Reference yield:

methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside (70774-92-4) → methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside (79297-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 1,2-dichloro-ethane / Heating

2: 68 percent / n-Bu₃SnH / toluene / Heating

With tri-n-butyl-tin hydride; In 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo00337a004

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + methyl 4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside (65530-28-1) → methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside (79297-68-0)

Guidance literature:

With pyridine;

DOI:10.1002/hlca.19540370147 DOI:10.1002/hlca.19460290101 DOI:10.1016/0008-6215(89)85078-5

upstream raw materials:

p-toluenesulfonyl chloride

methyl 4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

Imidazole-1-carbothioic acid O-[(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-(toluene-4-sulfonyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl] ester

methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside

Downstream raw materials:

(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine

(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine

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