(4aS,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3,4-dihydroxy-6-methyl-octahydro-naphthalen-2-one

Base Information

• Chemical Name: (4aS,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3,4-dihydroxy-6-methyl-octahydro-naphthalen-2-one
• CAS No.: 136655-25-9
• Molecular Formula: C₃₇H₅₄O₆Si
• Molecular Weight: 622.918
• Mol file: 136655-25-9.mol

Synonyms:

Chemical Property of (4aS,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3,4-dihydroxy-6-methyl-octahydro-naphthalen-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3,4-dihydroxy-6-methyl-octahydro-naphthalen-2-one

There total 1 articles about (4aS,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3,4-dihydroxy-6-methyl-octahydro-naphthalen-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:

(4aR,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-6-methyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one (135716-17-5) → (4aS,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3,4-dihydroxy-6-methyl-octahydro-naphthalen-2-one (135716-18-6,136655-25-9,136655-26-0)

Guidance literature:

With pyridine; osmium(VIII) oxide;

DOI:10.1016/0040-4039(91)80587-V

Reference yield:

(4aS,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3,4-dihydroxy-6-methyl-octahydro-naphthalen-2-one (135716-18-6,136655-25-9,136655-26-0) → N-((1S,2S,3S,6R)-2-{2-[(4R,6S)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl)-2,2-dimethyl-butyramide (135716-25-5)

Guidance literature:

Multi-step reaction with 9 steps

2: DiBAL / toluene / -78 °C

3: KHMDS / toluene

4: H₂ / 10percent Pd-C / methanol

5: Et₃N / CH₂Cl₂ / 0 °C

6: NaN₃ / dimethylformamide / 50 °C

7: H₂, Et₃N / 10percent Pd-C / ethanol; methanol

8: 76 percent / DMAP / pyridine

9: n-Bu₄NF / tetrahydrofuran

With dmap; sodium azide; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4039(91)80587-V

Reference yield:

(4aS,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3,4-dihydroxy-6-methyl-octahydro-naphthalen-2-one (135716-18-6,136655-25-9,136655-26-0) → [(4R,6R)-6-(2-{(1S,2S,3R,6S)-2-[(2,2-Dimethyl-butyrylamino)-methyl]-6-methyl-3-propyl-cyclohexyl}-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid (136491-82-2)

Guidance literature:

Multi-step reaction with 10 steps

2: DiBAL / toluene / -78 °C

3: KHMDS / toluene

4: H₂ / 10percent Pd-C / methanol

5: Et₃N / CH₂Cl₂ / 0 °C

6: NaN₃ / dimethylformamide / 50 °C

7: H₂, Et₃N / 10percent Pd-C / ethanol; methanol

8: 76 percent / DMAP / pyridine

9: n-Bu₄NF / tetrahydrofuran

10: 1) Dess-Martin periodinane, 2) 1.0 aq. KMnO₄, 5percent NaH₂PO₄ / t-BuOH, CH₂Cl₂

With dmap; potassium permanganate; sodium dihydrogenphosphate; sodium azide; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4039(91)80587-V

upstream raw materials:

(4aR,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-6-methyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

Downstream raw materials:

(4aS,7S,8S,8aS)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-octahydro-isochromen-3-one

2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

N-{(1S,2S,3S,6R)-2-[2-((2R,4R)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl}-2,2-dimethyl-butyramide

2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-{2-[(4R,6S)-6-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl ester