(4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one

Base Information

• Chemical Name: (4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one
• CAS No.: 916153-96-3
• Molecular Formula: C₂₁H₃₂O₅Si
• Molecular Weight: 392.568
• Mol file: 916153-96-3.mol

Synonyms:(4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one

Chemical Property of (4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one

There total 5 articles about (4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one 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: 74.0%

(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran (916154-05-7) → (4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one (916153-96-3)

Guidance literature:

With silica gel; pyridinium chlorochromate; In dichloromethane; at 45 ℃; for 6h;

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) → (4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one (916153-96-3)

Guidance literature:

Multi-step reaction with 2 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

With oxalyl dichloride; silica gel; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In dichloromethane; 1.1: Swern oxidation / 1.2: Wittig reaction;

DOI:10.1021/jo0615504

Reference yield:

3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal (913258-74-9) → (4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one (916153-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 78 percent / HF; pyridine / tetrahydrofuran / 0 - 20 °C

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

2.2: 75 percent / n-BuLi / CH₂Cl₂; hexane; tetrahydrofuran / 2 h / 20 °C

3.1: 74 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 6 h / 45 °C

With pyridine; oxalyl dichloride; hydrogen fluoride; silica gel; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Wittig reaction;

DOI:10.1021/jo0615504

upstream raw materials:

(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

3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal

1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose

Downstream raw materials:

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

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

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

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