benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside
• CAS No.: 501416-25-7
• Molecular Formula: C₂₆H₂₇NO₉S
• Molecular Weight: 529.568
• Mol file: 501416-25-7.mol

Synonyms:benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside

Chemical Property of benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside

There total 1 articles about benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside 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: 90.0%

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-galactopyranosyl bromide (53872-78-9) + 2-sulfanyl-1,3-benzoxazole (2382-96-9,118090-08-7) → benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside (501416-25-7)

Guidance literature:

With potassium carbonate; In acetone; toluene; at 20 ℃; for 16h;

DOI:10.1021/ol0273452

Reference yield: 76.0%

ethyl O-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside + benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside (501416-25-7) → ethyl O-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (953079-83-9)

Guidance literature:

With 3 A molecular sieve; silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 0.25h;

DOI:10.1016/j.tet.2007.07.036

Reference yield:

methyl 2,4-di-O-benzyl-6-O-(3-hydroxycarbonylpropanoyl)-α-D-glucopyranoside (1012044-74-4) + benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside (501416-25-7) → methyl 2,4-di-O-benzyl-3-O-(2-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranoside + methyl 2,4-di-O-benzyl-3-O-(2-O-benzyl-α-D-galactopyranosyl)-α-D-glucopyranoside (1012045-07-6)

Guidance literature:

methyl 2,4-di-O-benzyl-6-O-(3-hydroxycarbonylpropanoyl)-α-D-glucopyranoside; With dicyclohexyl-carbodiimide; In dichloromethane; for 72h;

benzoxazol-2-yl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-β-D-galactopyranoside; With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 96h;

With methanol; sodium methylate; In dichloromethane; at 20 ℃; for 48h; pH=8 - 9; Further stages.;

DOI:10.1021/jo701902f

upstream raw materials:

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

2-sulfanyl-1,3-benzoxazole

Downstream raw materials:

ethyl O-(2-O-benzyl-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

methyl 2,4-di-O-benzyl-3-O-(2-O-benzyl-α-D-galactopyranosyl)-α-D-glucopyranoside