Toluene-4-sulfonic acid (1R,2R)-2-benzyloxymethyl-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-but-3-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1R,2R)-2-benzyloxymethyl-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-but-3-enyl ester
• CAS No.: 245323-04-0
• Molecular Formula: C₃₇H₄₄O₆SSi
• Molecular Weight: 644.904
• Mol file: 245323-04-0.mol

Synonyms:Toluene-4-sulfonic acid (1R,2R)-2-benzyloxymethyl-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-but-3-enyl ester

Chemical Property of Toluene-4-sulfonic acid (1R,2R)-2-benzyloxymethyl-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1R,2R)-2-benzyloxymethyl-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-but-3-enyl ester

There total 6 articles about Toluene-4-sulfonic acid (1R,2R)-2-benzyloxymethyl-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-but-3-enyl 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: 81.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2R,3R,4S)-3-tosyloxy-4-benzyloxymethyl-5-hexene-1,2-diol (245323-03-9) → Toluene-4-sulfonic acid (1R,2R)-2-benzyloxymethyl-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-but-3-enyl ester (245323-04-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 10 ℃; for 9h;

DOI:10.1021/jo982130k

Reference yield:

(Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) → Toluene-4-sulfonic acid (1R,2R)-2-benzyloxymethyl-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-but-3-enyl ester (245323-04-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / PPh₃; Br₂; pyridine / benzene; CCl₄ / 2 h

2: 11 percent / Zn; aq. NH₄Cl / tetrahydrofuran / 1.5 h

3: pyridine

4: 1.7 g / TFA; H₂O / 5 h / 0 °C

5: 81 percent / imidazole / dimethylformamide / 9 h / 10 °C

With pyridine; 1H-imidazole; water; bromine; ammonium chloride; triphenylphosphine; trifluoroacetic acid; zinc; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide; benzene; 1: Substitution / 2: Addition / 3: Tosylation / 4: Hydrolysis / 5: Substitution;

DOI:10.1021/jo982130k

Reference yield:

benzyl bromide (100-39-0) → Toluene-4-sulfonic acid (1R,2R)-2-benzyloxymethyl-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-but-3-enyl ester (245323-04-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / NaH / tetrahydrofuran / 3.5 h / 50 °C

2: 83 percent / PPh₃; Br₂; pyridine / benzene; CCl₄ / 2 h

3: 11 percent / Zn; aq. NH₄Cl / tetrahydrofuran / 1.5 h

4: pyridine

5: 1.7 g / TFA; H₂O / 5 h / 0 °C

6: 81 percent / imidazole / dimethylformamide / 9 h / 10 °C

With pyridine; 1H-imidazole; water; bromine; sodium hydride; ammonium chloride; triphenylphosphine; trifluoroacetic acid; zinc; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide; benzene; 1: Alkylation / 2: Substitution / 3: Addition / 4: Tosylation / 5: Hydrolysis / 6: Substitution;

DOI:10.1021/jo982130k

upstream raw materials:

tert-butylchlorodiphenylsilane

(2R,3R,4S)-3-tosyloxy-4-benzyloxymethyl-5-hexene-1,2-diol

(Z)-4-benzyloxy-but-2-en-1-ol

benzyl bromide