methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-1-thio-β-D-glucopyranoside
CAS No.:122079-69-0
Molecular Formula:C₂₄H₂₉N₃O₅S
Molecular Weight:471.577
Hs Code.:

Synonyms:methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-1-thio-β-D-glucopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-1-thio-β-D-glucopyranoside

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Technology Process of methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-1-thio-β-D-glucopyranoside

There total 7 articles about methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-1-thio-β-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: 93.0%

: 122079-67-8
methyl 2,3-di-O-benzyl-6-O-propionyl-1-thio-4-O-tosyl-β-D-galactopyranoside

: 122079-69-0
methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-1-thio-β-D-glucopyranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 7h;
DOI:10.1016/0008-6215(89)84037-6

Reference yield: 83.0%

: 122079-68-9
methyl 2,3-di-O-benzyl-4-O-methanesulfonyl-6-O-propionyl-1-thio-β-D-galactopyranoside

: 122079-69-0
methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-1-thio-β-D-glucopyranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 120 ℃; for 6h;
DOI:10.1016/0008-6215(89)84037-6

Reference yield:

: 100-39-0
benzyl bromide

: 122079-69-0
methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) DMF, 2.) DMF, 0 deg C, then 3 h, room t.

2: 92 percent / aq. 60percent AcOH / 0.5 h / Heating

3: 70 percent / pyridine / 0 deg C, 8 h, then room t., 1 day

4: 91 percent / pyridine / 20 h / Ambient temperature

5: 83 percent / NaN₃ / dimethylformamide / 6 h / 120 °C

With pyridine; sodium azide; sodium hydride; acetic acid; In N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(89)84037-6