(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

Base Information

• Chemical Name: (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one
• CAS No.: 357439-43-1
• Molecular Formula: C₅₆H₆₆O₈Si₂
• Molecular Weight: 923.306
• Mol file: 357439-43-1.mol

Synonyms:(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

Chemical Property of (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

There total 6 articles about (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]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:

tert-butylchlorodiphenylsilane (58479-61-1) → (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one (357439-43-1)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 48 h / 30 °C

2: 91 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2.5 h / -5 °C

4: 1.58 g / (1S)-(+)-10-camphorsulfonic acid; p-anisaldehyde / toluene / 90 °C

With 2,6-dimethylpyridine; 4-methoxy-benzaldehyde; (+)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; toluene;

DOI:10.1016/j.tet.2004.07.010

Reference yield:

3-[4-benzyloxy-3-(4-methoxy-benzyloxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl]-1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-(2-hydroxy-1-hydroxymethyl-but-3-enyloxy)-propan-1-one (776315-70-9) → (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one (357439-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2.5 h / -5 °C

3: 1.58 g / (1S)-(+)-10-camphorsulfonic acid; p-anisaldehyde / toluene / 90 °C

With 2,6-dimethylpyridine; 4-methoxy-benzaldehyde; (+)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; toluene;

DOI:10.1016/j.tet.2004.07.010

Reference yield:

3-[4-benzyloxy-3-(4-methoxy-benzyloxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl]-1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-propan-1-one (357439-38-4) → (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one (357439-43-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 21.0 g / pyridinium p-toluenesulfonate / propan-1-ol / 16 h / 20 °C

2: 91 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2.5 h / -5 °C

4: 1.58 g / (1S)-(+)-10-camphorsulfonic acid; p-anisaldehyde / toluene / 90 °C

With 2,6-dimethylpyridine; pyridinium p-toluenesulfonate; 4-methoxy-benzaldehyde; (+)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In propan-1-ol; dichloromethane; water; toluene;

DOI:10.1016/j.tet.2004.07.010

upstream raw materials:

1-((3aR,8aS)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-[(2R,4S,5R)-2-(4-methoxy-phenyl)-4-vinyl-[1,3]dioxan-5-yloxy]-ethanone

tert-butyldiphenylsilyl triflate

tert-butylchlorodiphenylsilane

3-[4-benzyloxy-3-(4-methoxy-benzyloxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl]-1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-(2-hydroxy-1-hydroxymethyl-but-3-enyloxy)-propan-1-one

Downstream raw materials:

(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-ol

C₄₀H₄₄O₇S

C₄₁H₅₂O₉SSi

C₄₂H₄₅NO₉