(2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran
• CAS No.: 19139-89-0
• Molecular Formula: C₂₈H₃₁N₃O₅
• Molecular Weight: 489.571
• Mol file: 19139-89-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-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: 95.0%

Methanesulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (73111-13-4) → (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran (19139-89-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 90 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.carres.2009.05.022

Reference yield: 93.0%

methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside (114219-26-0) → (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran (19139-89-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.steroids.2013.11.022

Reference yield: 89.0%

methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (85716-43-4) → (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran (19139-89-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 10h; Inert atmosphere;

DOI:10.1080/00397911.2015.1005630

upstream raw materials:

Methanesulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

carbon monoxide

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

C₃₀H₃₃N₃O₅

methyl 6-deoxy-6-amino-2,3,4-tri-O-benzyl-α-D-glucopyranoside

(3R,4R,5R,6S,7R)-1-benzyl-4,5,6-tris(benzyloxy)-7-vinylazepan-3-ol

(3R,4R,5R,6S,7S)-1-benzyl-4,5,6-tris(benzyloxy)-7-vinylazepan-3-ol