benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

Base Information

Chemical Name:benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside
CAS No.:557104-56-0
Molecular Formula:C₁₇H₂₀O₅S
Molecular Weight:336.409
Hs Code.:

Synonyms:benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

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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 benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

Chemical Property:

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Technology Process of benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

There total 6 articles about benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-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: 75.0%

: 100-53-8
phenylmethanethiol

: 2873-29-2
D-glucal triacetate

: 557104-56-0
benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

Guidance literature:: With (1S)-10-camphorsulfonic acid; In dichloromethane; at 20 ℃; for 2h; stereoselective reaction;
DOI:10.1016/j.bmcl.2009.04.003

Reference yield:

: 100-53-8
phenylmethanethiol

: 2873-29-2
D-glucal triacetate

: 557104-56-0
benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

: benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-β-D-erythro-hex-2-enopyranoside

Guidance literature:: With gold(III) chloride; In dichloromethane; at 20 ℃; for 18h; optical yield given as %de;
DOI:10.1016/j.tet.2009.07.087

Reference yield:

: 4-methylphenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-1-thio-hex-2-enopyranoside

: 557104-56-0
benzyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -40 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / dichloromethane / 1 h / 0 °C

2.2: 1.5 h / -78 °C / Inert atmosphere

3.1: pyridine; dmap / dichloromethane / 1 h / 20 °C

4.1: bis(benzonitrile)palladium(II) chloride; 1,1'-bis-(diphenylphosphino)ferrocene / acetonitrile / 8 h / 90 °C / Inert atmosphere

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 1,1'-bis-(diphenylphosphino)ferrocene; bis(benzonitrile)palladium(II) chloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;
DOI:10.1021/acs.orglett.1c03302