(3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

Base Information

• Chemical Name: (3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol
• CAS No.: 923570-72-3
• Molecular Formula: C₃₅H₅₂O₄Si
• Molecular Weight: 564.881
• Mol file: 923570-72-3.mol

Synonyms:(3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

Chemical Property of (3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

There total 11 articles about (3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-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: 87.0%

(3aR,6R,7S,7aR)-7-[(tert-butyldiphenylsilyloxy)methyl]-3,3a,4,6,7,7a-hexahydro-7a-[3-(methoxymethoxy)propyl]-2,3,3,6-tetramethyl-5H-inden-5-one (607405-74-3) → (3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol (923570-72-3) + (3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol (607405-77-6)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 3h;

DOI:10.1021/jo062068o

Reference yield:

5-iodo-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-yl pivalate (923570-66-5) → (3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol (923570-72-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 83 percent / PPh₃; LiCl / Pd(CH₃CN)2Cl₂ / dimethylformamide / 24 h / 100 °C

2.1: thexylborane / tetrahydrofuran / 3 h / 0 °C

2.2: 85 percent / hydrogen peroxide; NaOH / tetrahydrofuran; H₂O / 1 h / 0 °C

3.1: 94 percent / ethyldiisopropylamine / CH₂Cl₂ / 20 °C

4.1: 94 percent / DIBAL-H / CH₂Cl₂; hexane / -78 °C

5.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

6.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

6.2: 61 percent / tetrahydrofuran; pentane / 4 h / -40 °C

7.1: 1 percent / KHMDS / tetrahydrofuran

8.1: 6 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -78 °C

With thexylborane; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; pentane; 1.1: Stille coupling / 5.1: Dess-Martin oxidation / 7.1: oxy-Cope rearrangement;

DOI:10.1021/jo062068o

Reference yield:

1,7,7-trimethyl-5-oxobicyclo[2.2.1]heptan-2-yl pivalate (923570-65-4) → (3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol (923570-72-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: hydrazine monohydrate; triethylamine / ethanol / 72 h / Heating

2.1: 27 g / iodine; 1,1,3,3-tetramethylquanidine / diethyl ether / 4 h / 20 °C

3.1: 83 percent / PPh₃; LiCl / Pd(CH₃CN)2Cl₂ / dimethylformamide / 24 h / 100 °C

4.1: thexylborane / tetrahydrofuran / 3 h / 0 °C

4.2: 85 percent / hydrogen peroxide; NaOH / tetrahydrofuran; H₂O / 1 h / 0 °C

5.1: 94 percent / ethyldiisopropylamine / CH₂Cl₂ / 20 °C

6.1: 94 percent / DIBAL-H / CH₂Cl₂; hexane / -78 °C

7.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

8.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

8.2: 61 percent / tetrahydrofuran; pentane / 4 h / -40 °C

9.1: 1 percent / KHMDS / tetrahydrofuran

10.1: 6 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -78 °C

With thexylborane; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; N,N,N',N'-tetramethylguanidine; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; pentane; 3.1: Stille coupling / 7.1: Dess-Martin oxidation / 9.1: oxy-Cope rearrangement;

DOI:10.1021/jo062068o

upstream raw materials:

(3aR,6R,7S,7aR)-7-[(tert-butyldiphenylsilyloxy)methyl]-3,3a,4,6,7,7a-hexahydro-7a-[3-(methoxymethoxy)propyl]-2,3,3,6-tetramethyl-5H-inden-5-one

5-iodo-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-yl pivalate

1,7,7-trimethyl-5-oxobicyclo[2.2.1]heptan-2-yl pivalate

2,2-Dimethyl-propionic acid (1S,2R,4S)-5-hydrazono-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester