methyl 2-acetamido-4-O-benzoyl-2,3-dideoxy-3-S-phenyl-3-thio-α-D-erythro-hex-5-enopyranoside

Base Information

Chemical Name:methyl 2-acetamido-4-O-benzoyl-2,3-dideoxy-3-S-phenyl-3-thio-α-D-erythro-hex-5-enopyranoside
CAS No.:86988-19-4
Molecular Formula:C₂₂H₂₃NO₅S
Molecular Weight:413.494
Hs Code.:

Synonyms:methyl 2-acetamido-4-O-benzoyl-2,3-dideoxy-3-S-phenyl-3-thio-α-D-erythro-hex-5-enopyranoside

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Chemical Property of methyl 2-acetamido-4-O-benzoyl-2,3-dideoxy-3-S-phenyl-3-thio-α-D-erythro-hex-5-enopyranoside

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Technology Process of methyl 2-acetamido-4-O-benzoyl-2,3-dideoxy-3-S-phenyl-3-thio-α-D-erythro-hex-5-enopyranoside

There total 5 articles about methyl 2-acetamido-4-O-benzoyl-2,3-dideoxy-3-S-phenyl-3-thio-α-D-erythro-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: 34.0%

: 86988-18-3
methyl 2-acetamido-4-O-benzoyl-2,6-dideoxy-6-iodo-3-S-phenyl-3-thio-α-D-allopyranoside

: 86988-19-4
methyl 2-acetamido-4-O-benzoyl-2,3-dideoxy-3-S-phenyl-3-thio-α-D-erythro-hex-5-enopyranoside

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 120h; Ambient temperature;
DOI:10.1016/0008-6215(83)88112-9

Reference yield:

: 86988-17-2
methyl 2-acetamido-4-O-benzoyl-6-bromo-2,6-dideoxy-3-S-phenyl-3-thio-α-D-allopyranoside

: 86988-19-4
methyl 2-acetamido-4-O-benzoyl-2,3-dideoxy-3-S-phenyl-3-thio-α-D-erythro-hex-5-enopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 67 percent / sodium iodide / dimethylformamide / 72 h / 90 °C / Heating

2: 34 percent / diazabicyclo<5.4.0>undec-5-ene / acetonitrile / 120 h / Ambient temperature

With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(83)88112-9

Reference yield:

: 88295-36-7
1-O-Methyl-2-N-acetylamino-2-deoxy-4,6-O-benzyliden-α,β-D-glucopyranosid

: 86988-19-4
methyl 2-acetamido-4-O-benzoyl-2,3-dideoxy-3-S-phenyl-3-thio-α-D-erythro-hex-5-enopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 1.) -20 deg C -> -5 deg C, 1 h; 2.) -5 de C, 1.5 h

2: 1.) 50 percent sodium hydride; 2.) sodium benzenethioxide / 1.) mineral oil, N,N-dimethylformamide, 2 h, r.t.; 2.) N,N-dimethylformamide, 0 deg C -> r.t., 12 h

3: 93 percent / N-bromosuccinimide, barium carbonate / CCl₄; various solvent(s) / 2 h / 80 °C

4: 67 percent / sodium iodide / dimethylformamide / 72 h / 90 °C / Heating

5: 34 percent / diazabicyclo<5.4.0>undec-5-ene / acetonitrile / 120 h / Ambient temperature

With N-Bromosuccinimide; sodium thiophenolate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; barium carbonate; sodium iodide; In pyridine; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(83)88112-9