(3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole

Base Information

• Chemical Name: (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole
• CAS No.: 764656-49-7
• Molecular Formula: C₃₄H₃₃NO₅
• Molecular Weight: 535.64
• Mol file: 764656-49-7.mol

Synonyms:(3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole

Chemical Property of (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole

There total 6 articles about (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole 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: 70.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + benzamide (55-21-0,27208-38-4) → (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole (764656-49-7)

Guidance literature:

With N-iodo-succinimide; In propiononitrile; at 45 ℃; for 2h; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/ejoc.201200130

Reference yield:

C13H15NO5 + benzyl bromide (100-39-0) → (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole (764656-49-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

DOI:10.1039/d0ob02477e

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + benzamide (55-21-0,27208-38-4) → 2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-O-2-N-(phenylmethan-yl-ylidene)-α-D-glucopyranose (459146-96-4) + (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole (764656-49-7)

Guidance literature:

3,4,6-tri-O-benzyl-D-glucal; benzamide; With N-iodo-succinimide; at -75 - 20 ℃; for 56h;

With 15-crown-6; sodium hydride; In dichloromethane; at 25 ℃; for 2h; Further stages.;

DOI:10.1016/j.tetlet.2004.06.082

upstream raw materials:

3,4,6-tri-O-benzyl-D-glucal

benzamide

benzonitrile

β-D-glucose pentaacetate