(S)-5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl ester

Base Information

• Chemical Name: (S)-5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl ester
• CAS No.: 345289-47-6
• Molecular Formula: C₂₃H₃₄O₆Si
• Molecular Weight: 434.605
• Mol file: 345289-47-6.mol

Synonyms:(S)-5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl ester

Chemical Property of (S)-5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl ester

There total 4 articles about (S)-5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl 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:

ethyl 3-lithiopropiolate (72036-30-7) → (S)-5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl ester (345289-47-6)

Guidance literature:

Multi-step reaction with 3 steps

1: O₃; PPh₃

3: Alpine borane

With Alpine borane; ozone; triphenylphosphine; 2: Swern oxidation;

DOI:10.1016/S0040-4039(01)00348-3

Reference yield:

(E)-ethyl 4-((2R,4S,5R)-5-(tert-butyldimethylsilyloxy)-2-phenyl-1,3-dioxan-4-yl)but-2-enoate → (S)-5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl ester (345289-47-6)

Guidance literature:

Multi-step reaction with 3 steps

1: O₃; PPh₃

3: Alpine borane

With Alpine borane; ozone; triphenylphosphine; 2: Swern oxidation;

DOI:10.1016/S0040-4039(01)00348-3

Reference yield:

5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl ester → (S)-5-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-4-hydroxy-pent-2-ynoic acid ethyl ester (345289-47-6)

Guidance literature:

Multi-step reaction with 2 steps

2: Alpine borane

With Alpine borane; 1: Swern oxidation;

DOI:10.1016/S0040-4039(01)00348-3

upstream raw materials:

ethyl 3-lithiopropiolate

Downstream raw materials:

Thiocarbonic acid O-[(2R,4S,5R)-4-((S)-5-oxo-2,5-dihydro-furan-2-ylmethyl)-2-phenyl-[1,3]dioxan-5-yl] ester O-phenyl ester