(2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran

Base Information

Chemical Name:(2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran
CAS No.:142436-65-5
Molecular Formula:C₂₅H₂₆O₃S
Molecular Weight:406.546
Hs Code.:

Synonyms:(2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran

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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 (2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran

Chemical Property:

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Technology Process of (2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran

There total 4 articles about (2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran 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: 93.0%

: 100-39-0
benzyl bromide

: 134614-93-0
Phenyl 2-deoxy-1-thio-α-D-threo-pentofuranoside

: 142436-65-5
(2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; 1.) 30 min, 2.) r.t., 18 h;
DOI:10.1021/jo00104a020

Reference yield: 54.0%

: 95990-87-7
1-O-Methyl-3,5-di-O-benzyl-2-deoxy-D-xylofuranose

: 108-98-5
thiophenol

: (2R,3R)-1,3-bis(benzyloxy)-5-methoxy-5-(phenylthio)pentan-2-ol

: 1428322-02-4
(2R,3R,5S)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran

: 142436-65-5
(2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran

Guidance literature:: 1-O-Methyl-3,5-di-O-benzyl-2-deoxy-D-xylofuranose; With dimethylboron bromide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

thiophenol; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 2h; Optical yield = 16.667 %de; chemoselective reaction; Mechanism; Inert atmosphere;
DOI:10.1021/jo3027438

Reference yield:

: 132620-67-8
Phenyl 3,5:6,7-di-O-isopropylidene-2-deoxy-1-thio-L-gluco-heptofuranoside

: 142436-65-5
(2R,3R,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

2: 93 percent / NaH / dimethylformamide / 1.) 30 min, 2.) r.t., 18 h

With sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1021/jo00104a020