(4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol

Base Information

• Chemical Name: (4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol
• CAS No.: 905312-42-7
• Molecular Formula: C₃₉H₇₂O₇Si₃
• Molecular Weight: 737.253
• Mol file: 905312-42-7.mol

Synonyms:(4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol

Chemical Property of (4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol

There total 1 articles about (4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol 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: 47.0%

vinyllithium (917-57-7) + (S)-2-<(triethylsilyl)oxy>-2-propanal (109170-83-4) + (4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone (581060-33-5) → (2S,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one (905312-41-6) + (4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol (905312-42-7)

Guidance literature:

vinyllithium; With copper(l) cyanide; In diethyl ether; at -78 - 0 ℃;

(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone; In diethyl ether; at -78 ℃; for 0.5h;

(S)-2-<(triethylsilyl)oxy>-2-propanal; With N,N,N,N,N,N-hexamethylphosphoric triamide; In diethyl ether; at -78 ℃; for 2h;

DOI:10.1016/j.tet.2006.04.079

Reference yield: 76.0%

(4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol (905312-42-7) → (2S,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one (905312-41-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 20 ℃; for 72h;

DOI:10.1016/j.tet.2006.04.079

Reference yield:

(4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol (905312-42-7) → N-benzyloxycarbonyl-(-)-actinobolin (581060-46-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 76 percent / acetic acid / tetrahydrofuran / 72 h / 20 °C

2.1: 87 percent / acetic acid; LiBH₄ / tetrahydrofuran / 0.17 h / 0 °C

3.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

4.1: 92 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

5.1: 86 percent / DDQ / acetonitrile; H₂O / 1 h / 0 - 20 °C

6.1: ozone / methanol / 0.1 h / -78 °C

6.2: 80 percent / Me₂S / methanol / 3 h / -78 - 20 °C

7.1: 83 percent / PDC; molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / 0 - 20 °C

8.1: 86 percent / NaN₃ / dimethylformamide / 4 h / 110 °C

9.1: HF; pyridine / acetonitrile / 0.17 h / 0 °C

10.1: (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / 2 h / -78 - 20 °C

10.2: 25.2 mg / silica gel / hexane; ethyl acetate

11.1: HCl; hydrogen / Pd/C / methanol; dioxane; H₂O / 18 h / 20 °C

11.2: 57 percent / DCC; Et₃N / dimethylformamide / 14 h / 20 °C

With pyridine; hydrogenchloride; dipyridinium dichromate; lithium borohydride; n-butyllithium; sodium azide; oxalyl dichloride; 4 A molecular sieve; hydrogen fluoride; hydrogen; ozone; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; 10.1: Swern oxidation;

DOI:10.1016/j.tet.2006.04.079

upstream raw materials:

vinyllithium

(S)-2-<(triethylsilyl)oxy>-2-propanal

(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone

Downstream raw materials:

(2S,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester