(2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS No.: 247257-17-6
• Molecular Formula: C₃₄H₂₈O₉S
• Molecular Weight: 612.657
• Mol file: 247257-17-6.mol

Synonyms:(2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Chemical Property of (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate

There total 16 articles about (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate 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: 97.0%

→ (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate (247257-17-6)

Guidance literature:

With sodium hydrogencarbonate; diothiothreitol; In N,N-dimethyl acetamide; at 20 ℃; for 1h;

Reference yield: 88.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) → (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate (247257-17-6)

Guidance literature:

With carbon disulfide; sodiumsulfide nonahydrate; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h; stereoselective reaction;

DOI:10.1021/jo302115k

Reference yield: 65.0%

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate (247257-17-6)

Guidance literature:

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside; With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 19 ℃; for 12h;

With carbon disulfide; sodiumsulfide nonahydrate; In N,N-dimethyl-formamide; at 19 ℃; for 0.25h;

DOI:10.1021/acs.orglett.8b02125

upstream raw materials:

triphenylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

tetraacetyl thioglucose

2,3,4,6-tetra-O-acetyl-1-S-trityl-1-thio-β-D-glucopyranose

S-trityl-1-thio-β-D-glucopyranose

Downstream raw materials:

1,2:3:4-di-O-isopropylidene-6-O-(tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactose

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

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