Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester

Base Information

• Chemical Name: Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester
• CAS No.: 900159-29-7
• Molecular Formula: C₂₇H₃₀O₄
• Molecular Weight: 418.533
• Mol file: 900159-29-7.mol

Synonyms:Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester

Chemical Property of Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester

There total 7 articles about Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl 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: 96.0%

Acetic acid (1R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-trityloxymethyl-butyl ester (900159-28-6) → Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester (900159-29-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo0605086

Reference yield:

(2R,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-1-trityloxy-pentan-2-ol (900159-10-6) → Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester (900159-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

2: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0605086

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → Acetic acid (1R,3S)-4-hydroxy-3-methyl-1-trityloxymethyl-butyl ester (900159-29-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 76 percent / pyridine / CH₂Cl₂ / Heating

2.1: n-BuLi; i-Pr₂NH / -15 °C

2.2: 81 percent / -78 °C

3.1: 100 percent / LiAlH₄ / tetrahydrofuran

4.1: 99 percent / imidazole / dimethylformamide / 2 h / 0 °C

5.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

6.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; triethylamine; diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0605086

upstream raw materials:

Acetic acid (1R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-trityloxymethyl-butyl ester

(2R,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-1-trityloxy-pentan-2-ol

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

trityl chloride

Downstream raw materials:

Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester

(R)-2-[(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethanol

(2S,3S,5R)-2-((R)-4-Benzenesulfonyl-6-benzyloxy-5-methyl-hexyl)-3-methyl-5-trityloxymethyl-tetrahydro-furan

(2S,3S,5R)-2-((S)-6-Benzyloxy-5-methyl-hexyl)-3-methyl-5-trityloxymethyl-tetrahydro-furan