Pentanedioic acid mono-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester

Base Information

• Chemical Name: Pentanedioic acid mono-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester
• CAS No.: 302594-69-0
• Molecular Formula: C₃₅H₄₀O₈
• Molecular Weight: 588.698
• Mol file: 302594-69-0.mol

Synonyms:Pentanedioic acid mono-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester

Chemical Property of Pentanedioic acid mono-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pentanedioic acid mono-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester

There total 2 articles about Pentanedioic acid mono-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester 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: 95.0%

glutaric anhydride, (108-55-4) + ((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol (223263-24-9) → Pentanedioic acid mono-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester (302594-69-0)

Guidance literature:

With dmap; In pyridine; at 60 ℃; for 3h;

DOI:10.1016/S0040-4039(00)01122-9

Reference yield:

9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol (194410-25-8) → Pentanedioic acid mono-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester (302594-69-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NaOMe / methanol

2: 95 percent / DMAP / pyridine / 3 h / 60 °C

With dmap; sodium methylate; In pyridine; methanol; 1: Hydrolysis / 2: Acylation;

DOI:10.1016/S0040-4039(00)01122-9

Reference yield: 84.0%

((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol (223263-24-9) + Pentanedioic acid mono-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester (302594-69-0) → Pentanedioic acid bis-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester (302594-70-3)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1016/S0040-4039(00)01122-9

upstream raw materials:

glutaric anhydride,

((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

9-O-acetyl-4,8-anhydro-5,6,7-tri-O-benzyl-1,2,3-trideoxy-D-glycero-D-galacto-non-1-enitol

Downstream raw materials:

Pentanedioic acid bis-((2R,3R,4R,5R,6R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester