1-p-tolyl-2,3,4-tri-O-benzyl-7-deoxy-7-diazo-1-thio-β-D-glucoheptopyran-6-ulose

Base Information

• Chemical Name: 1-p-tolyl-2,3,4-tri-O-benzyl-7-deoxy-7-diazo-1-thio-β-D-glucoheptopyran-6-ulose
• CAS No.: 1400906-85-5
• Molecular Formula: C₃₅H₃₄N₂O₅S
• Molecular Weight: 594.731

Synonyms:1-p-tolyl-2,3,4-tri-O-benzyl-7-deoxy-7-diazo-1-thio-β-D-glucoheptopyran-6-ulose

Chemical Property of 1-p-tolyl-2,3,4-tri-O-benzyl-7-deoxy-7-diazo-1-thio-β-D-glucoheptopyran-6-ulose

Chemical Property:

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Technology Process of 1-p-tolyl-2,3,4-tri-O-benzyl-7-deoxy-7-diazo-1-thio-β-D-glucoheptopyran-6-ulose

There total 2 articles about 1-p-tolyl-2,3,4-tri-O-benzyl-7-deoxy-7-diazo-1-thio-β-D-glucoheptopyran-6-ulose 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:

((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol (479252-05-6) → 1-p-tolyl-2,3,4-tri-O-benzyl-7-deoxy-7-diazo-1-thio-β-D-glucoheptopyran-6-ulose (1400906-85-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 2 h / 20 °C

2: oxalyl dichloride; 2,6-dimethylpyridine / toluene / 0 - 20 °C

3: toluene; diethyl ether / 1 h / -20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/jo300986c

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + C34H33ClO5S (1400906-89-9) → 1-p-tolyl-2,3,4-tri-O-benzyl-7-deoxy-7-diazo-1-thio-β-D-glucoheptopyran-6-ulose (1400906-85-5)

Guidance literature:

In diethyl ether; toluene; at -20 ℃; for 1h;

DOI:10.1021/jo300986c

Reference yield: 67.0%

methanol (67-56-1) + 1-p-tolyl-2,3,4-tri-O-benzyl-7-deoxy-7-diazo-1-thio-β-D-glucoheptopyran-6-ulose (1400906-85-5) → 1-p-tolyl-2,3,4-tri-O-benzyl-7-methyl-1-thio-β-D-glucoheptopyrano-6-ulose (1400907-04-1)

Guidance literature:

With copper acetylacetonate; In methanol; at 100 ℃; for 0.0833333h; Microwave irradiation;

DOI:10.1021/jo300986c

upstream raw materials:

diazomethane

C₃₄H₃₃ClO₅S

((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol

Downstream raw materials:

1-p-tolyl-2,3,4-tri-O-benzyl-7-methyl-1-thio-β-D-glucoheptopyrano-6-ulose

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