(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol
CAS No.:810670-86-1
Molecular Formula:C₃₀H₃₃NO₅S₂
Molecular Weight:551.728
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol

There total 2 articles about (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol 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:

: 2-thiazolinyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

: 810670-86-1
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 1h;
DOI:10.1021/ol048043y

Reference yield:

: 61236-94-0
4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride

: 810670-86-1
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 18-crown-6 / acetonitrile / 7 h / 20 °C

2: 155 mg / aq. NaOMe / methanol / 1 h / 20 °C

With 18-crown-6 ether; sodium methylate; In methanol; acetonitrile;
DOI:10.1021/ol048043y

Reference yield:

: 810670-86-1
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol

: 744246-05-7
2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

: 2-[(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylsulfanyl]-4,5-dihydro-thiazole

: 2-[(2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylsulfanyl]-4,5-dihydro-thiazole

Guidance literature:: (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4,5-dihydro-thiazol-2-ylsulfanyl)-tetrahydro-pyran-3-ol; With palladium(II) bromide; In 1,2-dichloro-ethane; at 20 ℃; for 2h;

2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside; With methyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at -40 - 20 ℃; for 6h;

With sodium cyanide; In acetone; at 20 ℃; for 16h; Title compound not separated from byproducts;
DOI:10.1021/ol048043y