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

Base Information

• Chemical Name: 2-thiazolinyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 744246-08-0
• Molecular Formula: C₂₂H₂₇NO₈S₂
• Molecular Weight: 497.59
• Mol file: 744246-08-0.mol

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

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

There total 2 articles about 2-thiazolinyl 3,4,6-tri-O-acetyl-2-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: 46.0%

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide (29741-69-3) + sodium 2-mercaptothiazolinate (71591-75-8) → Acetic acid (2R,3R,4S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-3,4-dihydro-2H-pyran-4-yl ester + Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-(2-thioxo-thiazolidin-3-yl)-tetrahydro-pyran-4-yl ester + 2-thiazolinyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-glucopyranoside (744246-08-0)

Guidance literature:

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

DOI:10.1002/anie.200454047

Reference yield: 46.0%

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide (29741-69-3) + sodium 2-mercaptothiazolinate (71591-75-8) → C22H27NO8S2 (744246-20-6) + Acetic acid (2R,3R,4S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-3,4-dihydro-2H-pyran-4-yl ester + 2-thiazolinyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-glucopyranoside (744246-08-0)

Guidance literature:

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

DOI:10.1002/chem.200600262

Reference yield: 75.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + 2-thiazolinyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-glucopyranoside (744246-08-0) → methyl 6-O-(3,4,6-tri-O-acetyl-2-O-benzyl-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:

With silver tetrafluoroborate; In 1,2-dichloro-ethane; for 0.333333h;

DOI:10.1016/j.tetlet.2007.12.105

upstream raw materials:

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide

sodium 2-mercaptothiazolinate

Downstream raw materials:

methyl 4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glycopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside

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