(2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide

Base Information

• Chemical Name: (2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide
• CAS No.: 339046-98-9
• Molecular Formula: C₂₈H₄₁NO₃Si
• Molecular Weight: 467.724
• Mol file: 339046-98-9.mol

Synonyms:(2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide

Chemical Property of (2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide

There total 4 articles about (2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide 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: 93.0%

3-(tert-butyl-dimethyl-silanyloxymethyl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-pent-4-enoic acid diethylamide (339046-87-6) → (2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide (339046-98-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 20 ℃;

DOI:10.1021/ja004325r

Reference yield:

(S)-(+)-β-vinyl-γ-butyrolactone (107080-45-5) → (2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide (339046-98-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / AlMe₃ / hexane; CH₂Cl₂ / 0 - 20 °C

2.1: 97 percent / imidazole; DMAP / CH₂Cl₂ / 18 h

3.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 79 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

4.1: 93 percent / PPTS / ethanol / 20 °C

With 1H-imidazole; dmap; n-butyllithium; trimethylaluminum; pyridinium p-toluenesulfonate; diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/ja004325r

Reference yield:

(S)-3-Hydroxymethyl-pent-4-enoic acid diethylamide (339046-99-0) → (2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide (339046-98-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / imidazole; DMAP / CH₂Cl₂ / 18 h

2.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 79 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

3.1: 93 percent / PPTS / ethanol / 20 °C

With 1H-imidazole; dmap; n-butyllithium; pyridinium p-toluenesulfonate; diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/ja004325r

upstream raw materials:

3-(tert-butyl-dimethyl-silanyloxymethyl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-pent-4-enoic acid diethylamide

(S)-(+)-β-vinyl-γ-butyrolactone

(S)-3-Hydroxymethyl-pent-4-enoic acid diethylamide

3-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid diethylamide

Downstream raw materials:

(4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one

4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline

4-{(4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-3,4,5,6-tetrahydro-pyridin-2-ylmethyl}-6-methoxy-quinoline

(3S,4R)-4-Azidomethyl-3-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-hex-5-enal