(2R,3R,4R,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-[(benzyloxy)-methyl]tetrahydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4R,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-[(benzyloxy)-methyl]tetrahydro-2H-pyran-3-ol
CAS No.:105139-04-6
Molecular Formula:C₂₇H₂₉N₃O₅
Molecular Weight:475.544
Hs Code.:

Synonyms:(2R,3R,4R,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-[(benzyloxy)-methyl]tetrahydro-2H-pyran-3-ol

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Chemical Property of (2R,3R,4R,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-[(benzyloxy)-methyl]tetrahydro-2H-pyran-3-ol

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Technology Process of (2R,3R,4R,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-[(benzyloxy)-methyl]tetrahydro-2H-pyran-3-ol

There total 4 articles about (2R,3R,4R,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-[(benzyloxy)-methyl]tetrahydro-2H-pyran-3-ol 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: 80.0%

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: 105139-04-6
(2R,3R,4R,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-[(benzyloxy)-methyl]tetrahydro-2H-pyran-3-ol

Guidance literature:: With sodium azide; ammonium cerium (IV) nitrate; water; In acetonitrile; at 20 ℃; for 0.0833333h; stereoselective reaction;
DOI:10.1021/jo200260w

Reference yield: 77.0%

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 105139-04-6
(2R,3R,4R,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-[(benzyloxy)-methyl]tetrahydro-2H-pyran-3-ol

Guidance literature:: 3,4,6-tri-O-benzyl-D-glucal; With 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; In dichloromethane; at -78 - -40 ℃; for 1.5h;

With methanol; triethylamine; In dichloromethane; at -40 - 23 ℃; for 2h;

With sodium azide; lithium perchlorate; In acetonitrile; at 0 - 23 ℃; for 12.5h; Further stages.;
DOI:10.1021/ja025639c

Reference yield: 72.0%

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 3,4,6-tri-O-benzyl-α-D-mannopyranosyl azide

: 105139-04-6
(2R,3R,4R,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-[(benzyloxy)-methyl]tetrahydro-2H-pyran-3-ol

Guidance literature:: 3,4,6-tri-O-benzyl-D-glucal; With 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1-dibenzotriazolo oxallate(DBTO); In dichloromethane; at -78 ℃; for 1h;

With methanol; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 0 ℃; for 1.33333h;

With sodium azide; lithium perchlorate; In acetonitrile; at 0 - 23 ℃; for 18.5h; Further stages.;
DOI:10.1021/ja025639c