(2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran
• CAS No.: 33639-74-6
• Molecular Formula: C₂₈H₃₂O₅
• Molecular Weight: 448.559
• Mol file: 33639-74-6.mol

Synonyms:(2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

Chemical Property of (2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

There total 13 articles about (2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 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: 96.7%

methyl 2,3,4-tri-O-benzyl-6-O-tosyl-α-D-mannopyranoside (65518-53-8) → methyl 2,3,4-tri-O-benzyl-α-D-rhamnopyranoside (33639-74-6,59055-57-1,67576-77-6,73174-44-4,73174-45-5,74841-88-6,83916-89-6,99212-28-9,73174-55-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; benzene; for 0.5h; Heating;

Reference yield: 75.7%

benzyl chloride (100-44-7) + methyl L-fucopyranoside (14687-15-1) → (2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran (33639-74-6)

Guidance literature:

With sodium hydride; at 100 ℃; for 5h; Molecular sieve;

DOI:10.1271/bbb.80609

Reference yield: 70.0%

methanol (67-56-1) + 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (167612-35-3) → (2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran (33639-74-6)

Guidance literature:

With iodine; for 4.5h;

DOI:10.1139/v03-062

upstream raw materials:

methanol

2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

benzyl bromide

phenyl 6-deoxy-1-thio-β-L-galactopyranoside

Downstream raw materials:

2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranose

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one

2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosyl (n-phenyl)trifluoroacetimidate