ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate

Base Information

• Chemical Name: ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate
• CAS No.: 220384-86-1
• Molecular Formula: C₂₅H₃₄O₅Si
• Molecular Weight: 442.627
• Mol file: 220384-86-1.mol

Synonyms:ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate

Chemical Property of ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate

There total 2 articles about ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate 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: 100.0%

benzaldehyde dimethyl acetal (1125-88-8) + ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate (220384-85-0) → ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate (220384-86-1)

Guidance literature:

With camphor-10-sulfonic acid; In benzene; for 1h; Heating;

DOI:10.1016/S0040-4039(98)02269-2

Reference yield:

(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-phenyl-but-2-enoic acid ethyl ester → ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate (220384-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 36 h / 20 °C

2: 95 percent / camphorsulfonic acid / benzene / 1 h / Heating

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

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

Reference yield: 99.0%

ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate (220384-86-1) → {(4S,5R)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2-phenyl-[1,3]dioxolan-4-yl}-methanol (220384-87-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(98)02269-2

upstream raw materials:

benzaldehyde dimethyl acetal

ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

Downstream raw materials:

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

(-)-8-epi-9-deoxygoniopypyrone

(1R,5R,7S,8S)-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

(1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-3,4-epoxy-1-phenylbutane