4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran

Base Information

• Chemical Name: 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran
• CAS No.: 135413-68-2
• Molecular Formula: C₃₇H₅₇FO₅Si
• Molecular Weight: 628.94
• Mol file: 135413-68-2.mol

Synonyms:

Chemical Property of 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran

There total 1 articles about 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran 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:

4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<1,2,6,7,8,8a(S)-hexahydro-8(S)-hydroxy-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran (79691-14-8,83348-89-4) + 1-chloromethyl-4-fluorobenzene (352-11-4) → 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran (79691-19-3,135413-68-2)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, RT, 2.) THF, DMF, reflux, 18 h;

DOI:10.1021/jm00112a024

Reference yield: 32.0%

4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran (79691-19-3,135413-68-2) → (4R,6R)-6-{2-[(1S,2S,6R,8S,8aR)-8-(4-Fluoro-benzyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-ethyl}-tetrahydro-pyran-2,4-diol + 4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-hydroxy-3,4,5,6-tetrahydro-2H-pyran (79691-20-6,135413-69-3)

Guidance literature:

With water; pyridinium p-toluenesulfonate; acetic acid; In tetrahydrofuran; for 65h; Ambient temperature;

DOI:10.1021/jm00112a024

Reference yield:

4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran (79691-19-3,135413-68-2) → 6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one (79691-18-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 32 percent / pyridinium tosylate (PPTS), acetic acid, H₂O / tetrahydrofuran / 65 h / Ambient temperature

2: 62 percent / CrO₃, pyridine / CH₂Cl₂ / 0.01 h / Ambient temperature

3: 99 percent / acetic acid, tetra-n-butylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature

With pyridine; chromium(VI) oxide; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00112a024

upstream raw materials:

4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<1,2,6,7,8,8a(S)-hexahydro-8(S)-hydroxy-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-<(tetrahydropyran-2-yl)oxy>-3,4,5,6-tetrahydro-2H-pyran

1-chloromethyl-4-fluorobenzene

Downstream raw materials:

4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-2-hydroxy-3,4,5,6-tetrahydro-2H-pyran

6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

4(R)-(tert-butyldimethylsiloxy)-6(R)-<2-<8(S)-<(4-fluorobenzyl)oxy>-1,2,6,7,8,8a(S)-hexahydro-2(S),6(R)-dimethyl-1(S)-naphthyl>ethyl>-3,4,5,6-tetrahydro-2H-pyran-2-one