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

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Chemical Name:(4S,5R)-5-((1R,2R,3R)-1,3-Bis-benzyloxy-3-phenyl-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid
CAS No.:917079-02-8
Molecular Formula:C₃₈H₅₂O₇Si
Molecular Weight:648.912
Hs Code.:

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

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

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

There total 14 articles about (4S,5R)-5-((1R,2R,3R)-1,3-Bis-benzyloxy-3-phenyl-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 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: 91.0%

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

: 917079-02-8
(4S,5R)-5-((1R,2R,3R)-1,3-Bis-benzyloxy-3-phenyl-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

Guidance literature:: With lithium hydroxide; In methanol; water; at 25 ℃; for 2h;
DOI:10.1016/j.tet.2006.09.005

Reference yield:

: 917078-93-4
(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal

: 917079-02-8
(4S,5R)-5-((1R,2R,3R)-1,3-Bis-benzyloxy-3-phenyl-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

Guidance literature:: Multi-step reaction with 6 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

6: 91 percent / lithium hydroxide monohydrate / methanol; H₂O / 2 h / 25 °C

With 2,6-dimethylpyridine; lithium hydroxide; methanesulfonamide; camphor-10-sulfonic acid; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In methanol; 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

: 917079-02-8
(4S,5R)-5-((1R,2R,3R)-1,3-Bis-benzyloxy-3-phenyl-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

Guidance literature:: Multi-step reaction with 5 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

5: 91 percent / lithium hydroxide monohydrate / methanol; H₂O / 2 h / 25 °C

With 2,6-dimethylpyridine; lithium hydroxide; methanesulfonamide; camphor-10-sulfonic acid; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In methanol; ethanol; dichloromethane; water; tert-butyl alcohol; 3: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tet.2006.09.005