methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-2,3,6-trideoxy-3-methylamino-α-D-threo-hex-5-enopyranoside

Base Information

Chemical Name:methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-2,3,6-trideoxy-3-methylamino-α-D-threo-hex-5-enopyranoside
CAS No.:109986-58-5
Molecular Formula:C₂₃H₂₅NO₆
Molecular Weight:411.455
Hs Code.:

Synonyms:methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-2,3,6-trideoxy-3-methylamino-α-D-threo-hex-5-enopyranoside

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Chemical Property of methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-2,3,6-trideoxy-3-methylamino-α-D-threo-hex-5-enopyranoside

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Technology Process of methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-2,3,6-trideoxy-3-methylamino-α-D-threo-hex-5-enopyranoside

There total 6 articles about methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-2,3,6-trideoxy-3-methylamino-α-D-threo-hex-5-enopyranoside 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: 71.0%

: 109986-57-4
methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-6-bromo-2,3,6-trideoxy-3-methylamino-α-D-arabino-hexopyranoside

: 109986-58-5
methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-2,3,6-trideoxy-3-methylamino-α-D-threo-hex-5-enopyranoside

Guidance literature:: With silver fluoride; In pyridine; at 25 ℃; for 18h;
DOI:10.1016/0008-6215(86)85062-5

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 109986-58-5
methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-2,3,6-trideoxy-3-methylamino-α-D-threo-hex-5-enopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: M sodium hydroxide / tetrahydrofuran / 1.) 0 deg C, 2 h; 2.) 25 deg C, 8 h

2: 1.) sodium hydride / 1.) DMF, 25 deg C, 0.5 h; 2.) DMF, 20 h

3: 75 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 3 h / Heating

4: 71 percent / silver fluoride / pyridine / 18 h / 25 °C

With sodium hydroxide; N-Bromosuccinimide; silver fluoride; sodium hydride; barium carbonate; In tetrahydrofuran; pyridine; tetrachloromethane;
DOI:10.1016/0008-6215(86)85062-5

Reference yield:

: 110043-59-9
methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-α-D-arabino-hexopyranoside

: 109986-58-5
methyl 4-O-benzoyl-3-N-benzyloxycarbonyl-2,3,6-trideoxy-3-methylamino-α-D-threo-hex-5-enopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: M sodium hydroxide / tetrahydrofuran / 24 h / 25 °C

2: M sodium hydroxide / tetrahydrofuran / 1.) 0 deg C, 2 h; 2.) 25 deg C, 8 h

3: 1.) sodium hydride / 1.) DMF, 25 deg C, 0.5 h; 2.) DMF, 20 h

4: 75 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 3 h / Heating

5: 71 percent / silver fluoride / pyridine / 18 h / 25 °C

With sodium hydroxide; N-Bromosuccinimide; silver fluoride; sodium hydride; barium carbonate; In tetrahydrofuran; pyridine; tetrachloromethane;
DOI:10.1016/0008-6215(86)85062-5