(S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

Base Information

• Chemical Name: (S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate
• CAS No.: 916154-08-0
• Molecular Formula: C₃₅H₅₂O₆Si
• Molecular Weight: 596.88
• Mol file: 916154-08-0.mol

Synonyms:(S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

Chemical Property of (S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

There total 9 articles about (S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate 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:

(3R,4R,5S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-hept-6-enoic acid + 2,4,6-trichlorobenzoyl chloride (4136-95-2) + (S)-hept-6-en-2-ol (88980-13-6) → (S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate (916154-08-0)

Guidance literature:

(3R,4R,5S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-hept-6-enoic acid; 2,4,6-trichlorobenzoyl chloride; With triethylamine; In tetrahydrofuran; at 20 ℃; for 1h;

(S)-hept-6-en-2-ol; With dmap; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1021/jo0615504

Reference yield:

(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran (916154-05-7) → (S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate (916154-08-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 74 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 6 h / 45 °C

2.1: 83 percent / methanol / 3 h / 20 °C / pH 9 - 10

3.1: 75 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h

4.1: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 12 h / 20 °C

5.1: triethylamine / tetrahydrofuran / 1 h / 20 °C

5.2: 400 mg / DMAP / tetrahydrofuran / 18 h / 20 °C

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; silica gel; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo0615504

Reference yield:

((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol (916154-04-6) → (S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate (916154-08-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 75 percent / n-BuLi / CH₂Cl₂; hexane; tetrahydrofuran / 2 h / 20 °C

2.1: 74 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 6 h / 45 °C

3.1: 83 percent / methanol / 3 h / 20 °C / pH 9 - 10

4.1: 75 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h

5.1: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 12 h / 20 °C

6.1: triethylamine / tetrahydrofuran / 1 h / 20 °C

6.2: 400 mg / DMAP / tetrahydrofuran / 18 h / 20 °C

With lithium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; silica gel; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Swern oxidation / 1.2: Wittig reaction;

DOI:10.1021/jo0615504

upstream raw materials:

2,4,6-trichlorobenzoyl chloride

(S)-hept-6-en-2-ol

(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol

Downstream raw materials:

(S)-hept-6-en-2-yl (3R,4S,5S)-5-benzyloxy-3-hydroxy-4-(p-methoxybenzyloxy)hept-6-enoate

(S)-hept-6-en-2-yl (3R,5S)-3-benzoyloxy-5-benzyloxy-4-oxo-hept-6-enoate

(S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate

(S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-(p-methoxybenzyloxy)hept-6-enoate

Refernces