4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranosyl chloride

Base Information

Chemical Name:4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranosyl chloride
CAS No.:71756-28-0
Molecular Formula:C₂₃H₂₆ClN₃O₅
Molecular Weight:459.93
Hs Code.:

Synonyms:4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranosyl chloride

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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 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranosyl chloride

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Technology Process of 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranosyl chloride

There total 13 articles about 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranosyl chloride 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: 72.0%

: Propionic acid (2S,3R,4S,5R,6S)-3-azido-4,5-bis-benzyloxy-6-hydroxy-tetrahydro-pyran-2-ylmethyl ester

: 71756-28-0
4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranosyl chloride

Guidance literature:: With thionyl chloride; at 20 ℃; for 15h;
DOI:10.1016/0040-4020(80)80148-7

Reference yield: 66.7%

: 71795-11-4
1-O-acetyl-4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranose

: 71756-28-0
4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranosyl chloride

: Propionic acid (2S,3R,4S,5R,6S)-3-azido-4,5-bis-benzyloxy-6-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With hydrogenchloride; In dichloromethane; 1.) -5 deg C, 2.) 20 deg C, 15 h;
DOI:10.1016/0040-4020(80)80148-7

Reference yield:

: 29388-46-3
methyl 2,3-di-O-benzyl-α-D-galactopyranoside

: 71756-28-0
4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-α-D-glucopyranosyl chloride

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 20 h / 20 °C

2: 91 percent / pyridine / 1.) -5 - 0 deg C, 10 min, 2.) 17 h, 20 deg C

3: 93.4 percent / sodium azide / dimethylformamide / 25 h / 140 - 160 °C

4: 95 percent / 80 percent AcOH aq. / 3 h / 80 °C

5: 98 percent / pyridine / 15 h / 20 °C

6: 75.5 percent / conc. H₂SO₄ / 0.5 h / 20 °C

7: 22.4 percent / HCl / CH₂Cl₂ / 1.) -5 deg C, 2.) 20 deg C, 15 h

With pyridine; hydrogenchloride; sodium azide; sulfuric acid; acetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(80)80148-7