(E)-methyl 4-((2S,3R,4S,5S,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)but-2-enoate

Base Information

• Chemical Name: (E)-methyl 4-((2S,3R,4S,5S,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)but-2-enoate
• CAS No.: 1270942-28-3
• Molecular Formula: C₃₉H₄₁N₃O₇
• Molecular Weight: 663.77
• Mol file: 1270942-28-3.mol

Synonyms:(E)-methyl 4-((2S,3R,4S,5S,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)but-2-enoate

Chemical Property of (E)-methyl 4-((2S,3R,4S,5S,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-methyl 4-((2S,3R,4S,5S,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)but-2-enoate

There total 1 articles about (E)-methyl 4-((2S,3R,4S,5S,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)but-2-enoate 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: 77.0%

(2S,3R,4S,5S,6R)-2-allyl-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran (1259515-58-6) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (E)-methyl 4-((2S,3R,4S,5S,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)but-2-enoate (1270942-28-3)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c0ob00555j

Reference yield: 60.0%

(E)-methyl 4-((2S,3R,4S,5S,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)but-2-enoate (1270942-28-3) → (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-1-oxa-7-azaspiro[5.5]undecan-8-one (1270942-32-9) + (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-1-oxa-7-azaspiro[5.5]undecan-8-one (1270942-31-8)

Guidance literature:

With 5% Pd-CaCO3; hydrogen; In methanol; at 20 ℃; under 760.051 Torr; optical yield given as %de;

DOI:10.1039/c0ob00555j

upstream raw materials:

(2S,3R,4S,5S,6R)-2-allyl-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran

acrylic acid methyl ester

Downstream raw materials:

(2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-1-oxa-7-azaspiro[5.5]undecan-8-one

(2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-1-oxa-7-azaspiro[5.5]undecan-8-one