((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-ylmethoxy)-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: ((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-ylmethoxy)-tert-butyl-diphenyl-silane
• CAS No.: 170707-20-7
• Molecular Formula: C₄₀H₅₂O₇Si
• Molecular Weight: 672.934
• Mol file: 170707-20-7.mol

Synonyms:((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-ylmethoxy)-tert-butyl-diphenyl-silane

Chemical Property of ((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-ylmethoxy)-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-ylmethoxy)-tert-butyl-diphenyl-silane

There total 1 articles about ((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-ylmethoxy)-tert-butyl-diphenyl-silane 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: 89.0%

2-Methoxypropene (116-11-0) + 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 (122822-08-6) → ((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-ylmethoxy)-tert-butyl-diphenyl-silane (170707-20-7)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 25 ℃; for 4h;

DOI:10.1021/ja00099a081

Reference yield: 97.0%

((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-ylmethoxy)-tert-butyl-diphenyl-silane (170707-20-7) → ((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)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 2h;

DOI:10.1021/ja00099a081 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-naphthacen-8-ylmethoxy)-tert-butyl-diphenyl-silane (170707-20-7) → {(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 (170707-27-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

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

3: 96 percent / CH₂Cl₂ / 5 h / 25 °C

4: 100 percent / H₂ / Pd(OH)2 / ethyl acetate / 48 h / 25 °C

5: 92 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 °C

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

7: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

8: 87 percent / CSA / CH₂Cl₂; methanol / 2 h / 0 °C

9: 94 percent / imidazole / dimethylformamide / 1 h / 0 °C

10: 96 percent / tetra-n-propylammonium perruthenate, NMO / acetonitrile / 1 h / 25 °C

11: 1.) zinc triflate, 2.) CSA / 1.) CH₂Cl₂, 25 deg C, 3 h, 2.) CH₂Cl₂, MeOH, 25 deg C, 1 h

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00146a010

upstream raw materials:

2-Methoxypropene

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

Downstream raw materials:

((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

(4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacene-8-carbaldehyde

(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

(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