ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Base Information

• Chemical Name: ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS No.: 187931-99-3
• Molecular Formula: C₂₁H₃₄O₅Si
• Molecular Weight: 394.583
• Mol file: 187931-99-3.mol

Synonyms:ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Chemical Property of ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

There total 8 articles about ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-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: 99.0%

2-Methoxypropene (116-11-0) + ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate (179618-34-9) → ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate (187931-99-3)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1016/S0040-4020(99)00794-2

Reference yield: 93.0%

2,2-dimethoxy-propane (77-76-9) + ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate (179618-34-9) → ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate (187931-99-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1002/hlca.201200656

Reference yield:

ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate (179618-33-8) → ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate (187931-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 14 h / 20 °C

2: 99 percent / camphorsulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

With methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; In dichloromethane; water; tert-butyl alcohol; 1: hydroxylation / 2: Cyclization;

DOI:10.1016/S0040-4020(99)00794-2

upstream raw materials:

2-Methoxypropene

ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate

ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate

(R)-Mandelic Acid

Downstream raw materials:

trimethyl (5S,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-3-phenylsulfonyl-7-phenylorthoheptanoate

ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate

{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

(+)-goniofufurone