2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: 2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 744246-05-7
• Molecular Formula: C₃₇H₃₉NO₅S₂
• Molecular Weight: 641.852
• Mol file: 744246-05-7.mol

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

Chemical Property of 2-thiazolinyl 2,3,4,6-tetra-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 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

There total 4 articles about 2-thiazolinyl 2,3,4,6-tetra-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: 83.0%

benzyl bromide (100-39-0) + 2-thiazolinyl 1-thio-β-D-glucopyranoside → 2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (744246-05-7)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1002/chem.200600262

Reference yield: 55.0%

tetra-O-benzyl glucopyranosyl chloride (25320-59-6) + sodium 2-mercaptothiazolinate (71591-75-8) → 2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (744246-05-7) + 3-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thiazolidine-2-thione

Guidance literature:

With 15-crown-5; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1002/anie.200454047

Reference yield:

1,3-thiazolin-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (142266-54-4) → 2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (744246-05-7)

Guidance literature:

Multi-step reaction with 2 steps

1: MeONa / methanol

2: NaOH / dimethylformamide

With sodium hydroxide; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/anie.200454047

upstream raw materials:

tetra-O-benzyl glucopyranosyl chloride

sodium 2-mercaptothiazolinate

benzyl bromide

1,3-thiazolin-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside

methyl (2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside