methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside

Base Information

• Chemical Name: methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside
• CAS No.: 131367-29-8
• Molecular Formula: C₂₁H₂₄N₂O₉
• Molecular Weight: 448.43

Synonyms:methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside

Chemical Property of methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside

Chemical Property:

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Technology Process of methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside

There total 1 articles about methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside 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: 45.0%

methyl 5,7,O-benzylidene-3-carbamonyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside (131367-26-5) + acetyl chloride (75-36-5) → methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside (131367-29-8)

Guidance literature:

In acetic anhydride; acetic acid; for 16h; Ambient temperature;

Reference yield: 78.0%

methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside (131367-29-8) + tert-butyl alcohol (75-65-0) → methyl 2,4-di-O-acetyl-5,7-O-benzylidene-3-tert-butoxycarbonylamino-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside (132867-55-1)

Guidance literature:

With lead(IV) acetate; In N,N-dimethyl-formamide; for 0.333333h; Heating;

DOI:10.1016/0008-6215(91)80151-C

Reference yield:

methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside (131367-29-8) → (methyl 5,7-O-benzylidene-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptano)<2,3-d>-oxazolidin-2-one (132867-64-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / lead tetra-acetate / dimethylformamide / 0.33 h / Heating

2: NaOMe / methanol / 0.5 h / -15 °C

With lead(IV) acetate; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)80151-C

upstream raw materials:

methyl 5,7,O-benzylidene-3-carbamonyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside

acetyl chloride

Downstream raw materials:

methyl 2,4-di-O-acetyl-5,7-O-benzylidene-3-tert-butoxycarbonylamino-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside

(methyl 5,7-O-benzylidene-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptano)<2,3-d>-oxazolidin-2-one

Acetic acid (3aR,4R,4aS,6R,8aR,10S,10aS)-3-acetyl-3a-cyano-10-methoxy-2-oxo-6-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-benzo[f]azulen-4-yl ester

methyl 3-C-acetamidomethyl-2,4-di-O-acetyl-5,7-O-benzylidene-3-tert-butoxycarbonylamino-3-deoxy-D-glycero-α-D-ido-heptoseptanoside

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