1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose

Base Information

• Chemical Name: 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose
• CAS No.: 150370-50-6
• Molecular Formula: C₃₄H₃₇NO₅
• Molecular Weight: 539.671
• Mol file: 150370-50-6.mol

Synonyms:1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose

Chemical Property of 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose

There total 22 articles about 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose 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%

2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl azide (150370-49-3) → 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose (150370-50-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h; Ambient temperature;

Reference yield: 95.0%

((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid allyl ester (566200-25-7) → 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranose (4132-27-8,85917-83-5,150370-50-6)

Guidance literature:

With palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; diethylamine; In water; acetonitrile; at 25 ℃; for 0.5h;

DOI:10.1021/ja049293c

Reference yield: 95.0%

((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid allyl ester → 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranose (4132-27-8,85917-83-5,150370-50-6)

Guidance literature:

((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid allyl ester; With diethylamine; In acetonitrile; at 25 ℃; for 0.0833333h;

With palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; In acetonitrile; at 25 ℃; for 0.5h;

DOI:10.1002/chem.200400503

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-α-D-glucose

2,3,4,6-tetra-O-benzyl-D-glucononitrile

((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid allyl ester

D-glucopyranosyl azide

Downstream raw materials:

ethyl (S)-3-(1,3-diisopropylureido)-4-oxo-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ylamino]butanoate

ethyl (R)-3-(1,3-diisopropylureido)-4-oxo-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ylamino]butanoate

C₄₀H₄₀BrNO₅

(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-N-(4-methoxyphenyl)tetrahydro-2H-pyran-2-amine

Refernces

• 1、 Bulman Page, Philip C.,Chan, Yohan,Liddle, John,Elsegood, Mark R.J.. "Carbohydrate-derived iminium salt organocatalysts for the asymmetric epoxidation of alkenes". . p. 7283 - 7305. Retrieved 2017/09/13.
• 2、 Nicolaou,Snyder, Scott A.,Nalbandian, Annie Z.,Longbottom, Deborah A.. "A new method for the stereoselective synthesis of α- and β-glycosylamines using the Burgess reagent". . p. 6234 - 6235. Retrieved 2007/10/03.