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

Base Information

• Chemical Name: 2-thiazolinyl 2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 810670-88-3
• Molecular Formula: C₃₀H₃₃NO₅S₂
• Molecular Weight: 551.728
• Mol file: 810670-88-3.mol

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

Chemical Property of 2-thiazolinyl 2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-thiazolinyl 2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

There total 1 articles about 2-thiazolinyl 2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 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:

3-O-acetyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride (89068-05-3) → 2-thiazolinyl 2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (810670-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 18-crown-6 / acetonitrile / 20 °C

2: 565 mg / aq. NaOMe / methanol / 20 °C

With 18-crown-6 ether; sodium methylate; In methanol; acetonitrile;

DOI:10.1021/ol048043y

Reference yield: 80.0%

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (74666-83-4,105990-37-2,125354-46-3,125354-47-4,125411-99-6,108739-67-9) + 2-thiazolinyl 2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (810670-88-3) → 2-thiazolinyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In 1,2-dichloro-ethane; at -20 - 20 ℃;

DOI:10.1016/j.tetasy.2004.11.029

Reference yield:

2-thiazolinyl 2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (810670-88-3) + 2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (744246-05-7) → 2-[(2S,3R,4S,5R,6R)-3,5-Bis-benzyloxy-6-benzyloxymethyl-4-((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)-3,5-Bis-benzyloxy-6-benzyloxymethyl-4-((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:

2-thiazolinyl 2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside; 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 20h;

With sodium cyanide; In acetone; at 20 ℃; for 16h; Title compound not separated from byproducts;

DOI:10.1021/ol048043y

upstream raw materials:

3-O-acetyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride