(2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol
• CAS No.: 676328-26-0
• Molecular Formula: C₅₉H₆₆O₁₁
• Molecular Weight: 951.166
• Mol file: 676328-26-0.mol

Synonyms:(2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol

Chemical Property of (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol

There total 2 articles about (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol 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: 92.0%

Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester → (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol (676328-26-0)

Guidance literature:

With sodium methylate; In methanol; dichloromethane;

DOI:10.1055/s-2003-44999

Reference yield:

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (125392-62-3) → (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol (676328-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Yb(OTf)3; N-iodosuccinimide / CH₂Cl₂ / 0 °C

2: 92 percent / NaOMe / methanol; CH₂Cl₂

With N-iodo-succinimide; sodium methylate; ytterbium(III) triflate; In methanol; dichloromethane;

DOI:10.1055/s-2003-44999

Reference yield:

((3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-ylmethoxy)-tert-butyl-dimethyl-silane + (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol (676328-26-0) → benzoic acid 4,5-bis-benzyloxy-2-[4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:

With N-iodo-succinimide; ytterbium(III) triflate; In dichloromethane; at 0 ℃;

DOI:10.1055/s-2003-44999

upstream raw materials:

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)