phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside

Base Information

Chemical Name:phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside
CAS No.:241490-66-4
Molecular Formula:C₂₀H₂₅NO₃S
Molecular Weight:359.489
Hs Code.:

Synonyms:phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside

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Chemical Property of phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside

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Technology Process of phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside

There total 2 articles about phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside 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: 42.0%

: 917-54-4
methyllithium

: O-benzyl phenyl-2,6-dideoxy-1-thio-α,β-erythro-hexopyranosid-3-ulose oxime

: 241490-66-4
phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside

: 241490-67-5
phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside

Guidance literature:: methyllithium; With cerium(III) chloride; In tetrahydrofuran; diethyl ether; at -78 ℃;

O-benzyl phenyl-2,6-dideoxy-1-thio-α,β-erythro-hexopyranosid-3-ulose oxime; In tetrahydrofuran; diethyl ether; at -78 - -50 ℃;
DOI:10.1021/jo990403l

Reference yield:

: 1,5-anhydro-4-O-(2-naphthyl)methyl-2,6-dideoxy-L-erythro-hex-1-en-3-ulose

: 917-54-4
methyllithium

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 108-98-5
thiophenol

: 241490-66-4
phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-α-ribo-hexopyranoside

: 241490-67-5
phenyl 3-(O-benzylhydroxyamino)-2,3,6-trideoxy-3-C-methyl-1-thio-β-ribo-hexopyranoside

Guidance literature:: 1,5-anhydro-4-O-(2-naphthyl)methyl-2,6-dideoxy-L-erythro-hex-1-en-3-ulose; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 23 ℃; for 2h; Inert atmosphere;

thiophenol; With pyridine; triethylamine; In dichloromethane; water; for 5h; Inert atmosphere;

methyllithium; O-benzylhydoxylamine hydrochloride; Overall yield = 64 percent; Overall yield = 0.332 g; diastereoselective reaction; Further stages;
DOI:10.1021/acs.orglett.9b03812