(3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-one

Base Information

• Chemical Name: (3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-one
• CAS No.: 389086-09-3
• Molecular Formula: C₄₄H₇₄O₇S₂Si₂
• Molecular Weight: 835.37
• Mol file: 389086-09-3.mol

Synonyms:(3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-one

Chemical Property of (3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-one

There total 13 articles about (3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-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: 98.0%

(R)-4-benzyloxy-2-(triethysilyloxy)butanal (389085-92-1) + (S)-3-(4-methoxybenzyl)oxy-5-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}-pentan-2-one (389085-91-0) → (3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-one (389086-09-3)

Guidance literature:

(S)-3-(4-methoxybenzyl)oxy-5-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}-pentan-2-one; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1.66667h;

(R)-4-benzyloxy-2-(triethysilyloxy)butanal; In tetrahydrofuran; hexane; at -78 - -50 ℃; for 1.5h;

DOI:10.1016/S0040-4020(02)01379-0

Reference yield:

triethylsilyl chloride (994-30-9) → (3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-one (389086-09-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: 87 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / 2 h / -78 - -20 °C

3.1: 92 percent / pyridine*SO₃; Et₃N / dimethylsulfoxide / 1.25 h / 20 °C

4.1: 92 percent / tetrahydrofuran; diethyl ether / 2 h / -78 - -50 °C

5.1: 93 percent / SO₃*pyridine; Et₃N / dimethylsulfoxide / 1.25 h / 20 °C

6.1: nBuLi; HMDS; ZnCl₂ / hexane; tetrahydrofuran / 1.67 h / -78 - 0 °C

6.2: 98 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

With 1H-imidazole; n-butyllithium; pyridine-SO₃ complex; sulfur trioxide pyridine complex; diisobutylaluminium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 3.1: Parikh-Doering oxidation / 5.1: Parikh-Doering oxidation;

DOI:10.1016/S0040-4020(02)01379-0

Reference yield:

(S)-4-[2-(4-hydroxybutyl)-1,3-dithian-2-yl]-butane-1,2-diol (389086-04-8) → (3S,7R)-9-benzyloxy-6-hydroxy-3-(4-methoxybenzyl)oxy-7-triethylsilyloxy-1-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}nonan-4-one (389086-09-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 75 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / 20 °C

2.1: 98 percent / imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 87 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / 2 h / -78 - -20 °C

4.1: 92 percent / pyridine*SO₃; Et₃N / dimethylsulfoxide / 1.25 h / 20 °C

5.1: 92 percent / tetrahydrofuran; diethyl ether / 2 h / -78 - -50 °C

6.1: 93 percent / SO₃*pyridine; Et₃N / dimethylsulfoxide / 1.25 h / 20 °C

7.1: nBuLi; HMDS; ZnCl₂ / hexane; tetrahydrofuran / 1.67 h / -78 - 0 °C

7.2: 98 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

With 1H-imidazole; n-butyllithium; pyridine-SO₃ complex; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 4.1: Parikh-Doering oxidation / 6.1: Parikh-Doering oxidation;

DOI:10.1016/S0040-4020(02)01379-0

upstream raw materials:

(R)-4-benzyloxy-2-(triethysilyloxy)butanal

(S)-3-(4-methoxybenzyl)oxy-5-{2-[4-(triethylsilyloxy)butyl]-1,3-dithian-2-yl}-pentan-2-one

triethylsilyl chloride

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

Acetic acid (S)-1-((R)-3-benzyloxy-1-triethylsilanyloxy-propyl)-4-(4-methoxy-benzyloxy)-3-oxo-6-[2-(4-triethylsilanyloxy-butyl)-[1,3]dithian-2-yl]-hexyl ester

C₇₉H₁₃₀O₁₁S₂Si₄

1-[10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyl)oxy-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-5-(tert-butyldimethylsilyl)oxy-5-[5-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylpentan-2-one

2-[2-(benzyloxy)ethyl]-5-(tert-butyldimethylsilyl)oxy-10-[2-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyloxymethyl)-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadecane