(2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((E)-prop-1-enyl)tetrahydro-2H-pyran

Base Information

• Chemical Name: (2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((E)-prop-1-enyl)tetrahydro-2H-pyran
• CAS No.: 194980-06-8
• Molecular Formula: C₃₇H₄₀O₅
• Molecular Weight: 564.722
• Mol file: 194980-06-8.mol

Synonyms:(2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((E)-prop-1-enyl)tetrahydro-2H-pyran

Chemical Property of (2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((E)-prop-1-enyl)tetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((E)-prop-1-enyl)tetrahydro-2H-pyran

There total 6 articles about (2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((E)-prop-1-enyl)tetrahydro-2H-pyran 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: 84.0%

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene (82659-59-4) → (2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((E)-prop-1-enyl)tetrahydro-2H-pyran (194980-06-8)

Guidance literature:

cyclooctadiene-bis(methyldiphenylphosphine)-iridium hexafluorophosphate; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/ol060671n

Reference yield:

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene (82659-59-4) → 2,3,4,6-tetra-O-benzyl-1-((Z)-prop-1-en-1-yl)-α-D-mannopyranose + (2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((E)-prop-1-enyl)tetrahydro-2H-pyran (194980-06-8)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; In benzene; for 48h; Reflux;

Reference yield:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → (2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-((E)-prop-1-enyl)tetrahydro-2H-pyran (194980-06-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Cooling with ice

1.2: 20 °C / Cooling with ice

2.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0 - 20 °C

3.1: bis(benzonitrile)palladium(II) dichloride / toluene / 90 °C / Inert atmosphere

With bis(benzonitrile)palladium(II) dichloride; trimethylsilyl trifluoromethanesulfonate; sodium hydride; In N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;

upstream raw materials:

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene

2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

benzyl bromide

Downstream raw materials:

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

1-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)formic acid

{(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid