(4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate

Base Information

• Chemical Name: (4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate
• CAS No.: 917078-98-9
• Molecular Formula: C₄₀H₅₆O₇Si
• Molecular Weight: 676.966
• Mol file: 917078-98-9.mol

Synonyms:(4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate

Chemical Property of (4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate

There total 13 articles about (4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate 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:

(4R,5R,6R)-ethyl-4,6-bis(benzyloxy)-2,3-dihydroxy-6-phenyl-5-(triisopropylsilanyloxy)-hexanoate + 2,2-dimethoxy-propane (77-76-9) → (4R,5S)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate + (4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate (917078-98-9)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2006.09.005

Reference yield:

(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal (917078-93-4) → (4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate (917078-98-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / CH₂Cl₂ / 2 h / 20 °C

2: 72 percent / K₂CO₃ / ethanol / 1 h / 20 °C

3: 98 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

4: 92 percent / AD-mix β; (DHQD)2PHAL; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

5: CSA / CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; methanesulfonamide; camphor-10-sulfonic acid; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In ethanol; dichloromethane; water; tert-butyl alcohol; 1: Wittig olefination / 4: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tet.2006.09.005

Reference yield:

(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formyloxy-6-phenyl-2-hexenoate → (4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate (917078-98-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / K₂CO₃ / ethanol / 1 h / 20 °C

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

3: 92 percent / AD-mix β; (DHQD)2PHAL; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

4: CSA / CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; methanesulfonamide; camphor-10-sulfonic acid; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In ethanol; dichloromethane; water; tert-butyl alcohol; 3: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tet.2006.09.005

upstream raw materials:

2,2-dimethoxy-propane

(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal

(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate

(E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester

Downstream raw materials:

methyl 2-((4R,5S)-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl)acetate

1-[5-(1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-diazo-ethanone

5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one

(4S,5R)-5-((1R,2R,3R)-1,3-Bis-benzyloxy-3-phenyl-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid