methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-α-D-allopyranoside

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Chemical Name:methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-α-D-allopyranoside
CAS No.:128854-92-2
Molecular Formula:C₁₄H₁₅BrFN₃O₄
Molecular Weight:388.193
Hs Code.:

Synonyms:methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-α-D-allopyranoside

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Chemical Property of methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-α-D-allopyranoside

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Technology Process of methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-α-D-allopyranoside

There total 8 articles about methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-α-D-allopyranoside 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: 81.5%

: 128854-91-1
methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-2-fluoro-α-D-allopyranoside

: methyl 3-azido-6-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-allopyranoside

: 128854-92-2
methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-α-D-allopyranoside

Guidance literature:: With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 1h; Heating;
DOI:10.1016/0008-6215(90)84168-T

Reference yield:

: 31077-89-1
1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose

: 128854-92-2
methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / 45percent HBr / CHCl₃; acetic acid / 3 h / 25 °C

2: Bu₄NBr, ethyldiisopropylamine / CH₂Cl₂ / 48 h / 55 °C / molecular sieve 4A

3: 0.025M NaOCH₃ / 1 h / 25 °C

4: 93 percent / p-toluenesulfonic acid / acetonitrile / 1 h

5: 94 percent / pyridine / CH₂Cl₂ / 0.25 h / -10 °C

6: 67 percent / LiN₃ / dimethylformamide / 13 h / 75 °C

7: 81.5 percent / NBS, BaCO₃ / CCl₄ / 1 h / Heating

With pyridine; N-Bromosuccinimide; lithium azide; tetrabutylammomium bromide; hydrogen bromide; sodium methylate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; barium carbonate; In tetrachloromethane; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(90)84168-T

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 128854-92-2
methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / p-toluenesulfonic acid / acetonitrile / 1 h

2: 94 percent / pyridine / CH₂Cl₂ / 0.25 h / -10 °C

3: 67 percent / LiN₃ / dimethylformamide / 13 h / 75 °C

4: 81.5 percent / NBS, BaCO₃ / CCl₄ / 1 h / Heating

With pyridine; N-Bromosuccinimide; lithium azide; toluene-4-sulfonic acid; barium carbonate; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(90)84168-T