(4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol

Base Information

• Chemical Name: (4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol
• CAS No.: 170707-22-9
• Molecular Formula: C₃₅H₅₀O₇Si
• Molecular Weight: 610.863

Synonyms:(4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol

Chemical Property of (4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol

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Technology Process of (4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol

There total 7 articles about (4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-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: 95.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-(3-Hydroxy-propyl)-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol (159328-05-9) → (4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol (170707-22-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 6h;

DOI:10.1021/ja00099a081

Reference yield:

((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-methanol (170707-21-8) → (4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol (170707-22-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂

2: 96 percent / CH₂Cl₂ / 5 h / 25 °C

3: 100 percent / H₂ / Pd(OH)2 / ethyl acetate / 48 h / 25 °C

4: 92 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 °C

5: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 6 h / 25 °C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/ja00146a010

Reference yield:

(4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacene-8-carbaldehyde (159328-02-6) → (4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol (170707-22-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / CH₂Cl₂ / 5 h / 25 °C

2: 100 percent / H₂ / Pd(OH)2 / ethyl acetate / 48 h / 25 °C

3: 92 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 °C

4: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 6 h / 25 °C

With dmap; lithium aluminium tetrahydride; hydrogen; triethylamine; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/ja00146a010

upstream raw materials:

tert-butylchlorodiphenylsilane

(4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-8-(3-Hydroxy-propyl)-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-10-ol

2,6:5,9:8,12-Trianhydro-4-O-benzyl-1-O-(tert-butyldiphenylsilyl)-3,7,10-trideoxy-5-C-methyl-D-allo-D-altro-tridecitol

3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Hydroxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propionic acid methyl ester

Downstream raw materials:

(4aR,5aS,6aR,8R,10S,10aR,11aR,12aS)-10-(tert-Butyl-dimethyl-silanyloxy)-8-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacene

(2R,3S,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-hydroxymethyl-10a-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol

{(2R,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-10a-methyl-decahydro-1,8,10-trioxa-anthracen-2-yl}-methanol

(2R,4aR,5S,7R,8aR,9aS,10aR)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-10a-methyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde

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