(2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile

Base Information

• Chemical Name: (2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile
• CAS No.: 188819-43-4
• Molecular Formula: C₃₅H₃₅NO₅
• Molecular Weight: 549.667
• Mol file: 188819-43-4.mol

Synonyms:(2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile

Chemical Property of (2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile

There total 8 articles about (2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile 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: 56.0%

trimethylsilyl cyanide (7677-24-9) + 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose (3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-68-4,83462-69-5,94943-10-9) → 1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl cyanide (188819-44-5) + (2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile (188819-43-4)

Guidance literature:

With zinc trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.201800090

Reference yield: 51.0%

trimethylsilyl cyanide (7677-24-9) + 2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose (3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-69-5,94943-10-9,83462-68-4) → 1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl cyanide (188819-44-5) + (2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile (188819-43-4)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 0 - 20 ℃; for 0.583333h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b00948

Reference yield: 49.0%

trimethylsilyl cyanide (7677-24-9) + 2,3,4,6-tetra-O-benzyl-1-O-1',3'2'-dioxaphosphacyclohexane-α,β-D-mannopyranosyl-2-oxide → 1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl cyanide (188819-44-5) + (2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile (188819-43-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃;

DOI:10.1016/S0957-4166(01)00305-6

upstream raw materials:

trimethylsilyl cyanide

S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside

2-S-(2,3,4,6-Tetra-O-benzyl-α-D-mannopyranosyl)-2-oxo-5,5-dimethyl-1,3,2-dioxaphosphorinane

2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

(Z)-3-Amino-3-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester