(S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester
• CAS No.: 187402-09-1
• Molecular Formula: C₆₂H₆₈O₁₃
• Molecular Weight: 1021.21
• Mol file: 187402-09-1.mol

Synonyms:(S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester

Chemical Property of (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester

There total 3 articles about (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl 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:

benzaldehyde dimethyl acetal (1125-88-8) → (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester (187402-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / CSA / acetonitrile / 0.75 h / 35 °C

2: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 2 h, 2.) DME, r.t., 2 h

With camphor-10-sulfonic acid; di(n-butyl)tin oxide; cesium fluoride; In acetonitrile;

DOI:10.1002/chem.19970031006

Reference yield:

(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol (172147-75-0) → (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester (187402-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / CSA / acetonitrile / 0.75 h / 35 °C

2: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 2 h, 2.) DME, r.t., 2 h

With camphor-10-sulfonic acid; di(n-butyl)tin oxide; cesium fluoride; In acetonitrile;

DOI:10.1002/chem.19970031006

Reference yield:

benzyl (R)-(+)-3-phenyl-2-(trifluoromethylsulfonyloxy)propanoate (111437-25-3) + (2S,4aR,6R,7R,8R,8aR)-2-Phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (187402-06-8) → (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester (187402-09-1)

Guidance literature:

With di(n-butyl)tin oxide; cesium fluoride; Yield given. Multistep reaction; 1.) MeOH, reflux, 2 h, 2.) DME, r.t., 2 h;

DOI:10.1002/chem.19970031006

upstream raw materials:

benzyl (R)-(+)-3-phenyl-2-(trifluoromethylsulfonyloxy)propanoate

(2S,4aR,6R,7R,8R,8aR)-2-Phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

benzaldehyde dimethyl acetal

(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol