(3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-(methoxymethoxy)-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate

Base Information

• Chemical Name: (3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-(methoxymethoxy)-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate
• CAS No.: 923570-95-0
• Molecular Formula: C₃₉H₅₆O₅Si
• Molecular Weight: 632.956
• Mol file: 923570-95-0.mol

Synonyms:(3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-(methoxymethoxy)-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate

Chemical Property of (3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-(methoxymethoxy)-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-(methoxymethoxy)-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate

There total 26 articles about (3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-(methoxymethoxy)-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate 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: 90.0%

(3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxy-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate (923570-94-9) + chloromethyl methyl ether (107-30-2) → (3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-(methoxymethoxy)-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate (923570-95-0)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jo062068o

Reference yield:

5-iodo-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-yl pivalate (923570-66-5) → (3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-(methoxymethoxy)-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate (923570-95-0)

Guidance literature:

Multi-step reaction with 22 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: 44 percent / KHMDS / tetrahydrofuran

8.1: 84 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -78 °C

9.1: 93 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 20 °C

10.1: 81 percent / 9-BBNBr / CH₂Cl₂ / 3 h / -40 °C

11.1: 75 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

12.1: 25 percent / molecular sieves 4 Angstroem; EtAlCl₂ / CH₂Cl₂; hexane / 3 h / -78 °C

13.1: 97 percent / potassium hydride; n-Bu₄NI / tetrahydrofuran; various solvent(s) / 50 °C

14.1: 45 percent / OsO₄; N-methylmorpholine N-oxide; buffer / tetrahydrofuran; 2-methyl-propan-2-ol / 96 h / 20 °C / pH 7

15.1: 98 percent / sodium periodate / tetrahydrofuran; H₂O / 48 h

16.1: 25 percent / sodium borohydride / ethanol / 20 °C

17.1: 85 percent / pyridine; DMAP / CH₂Cl₂ / 20 °C

18.1: 53 percent / Oxone; silica gel / CH₂Cl₂ / 2 h / 20 °C

19.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

20.1: 85 percent / DBU / CH₂Cl₂ / 20 °C

21.1: 85 percent / sodium borohydride / ethanol / 4 h / 20 °C

22.1: 90 percent / ethyldiisopropylamine; DMAP / CH₂Cl₂ / 20 °C

With pyridine; B-Br-9-BBN; dmap; Oxone; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 4 A molecular sieve; thexylborane; tert.-butyl lithium; ethylaluminum dichloride; silica gel; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; 1.1: Stille coupling / 5.1: Dess-Martin oxidation / 7.1: oxy-Cope rearrangement / 11.1: Dess-Martin oxidation / 12.1: ene reaction / 19.1: Dess-Martin oxidation;

DOI:10.1021/jo062068o

Reference yield:

1,7,7-trimethyl-5-oxobicyclo[2.2.1]heptan-2-yl pivalate (923570-65-4) → (3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-(methoxymethoxy)-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate (923570-95-0)

Guidance literature:

Multi-step reaction with 24 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: 44 percent / KHMDS / tetrahydrofuran

10.1: 84 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -78 °C

11.1: 93 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 20 °C

12.1: 81 percent / 9-BBNBr / CH₂Cl₂ / 3 h / -40 °C

13.1: 75 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

14.1: 25 percent / molecular sieves 4 Angstroem; EtAlCl₂ / CH₂Cl₂; hexane / 3 h / -78 °C

15.1: 97 percent / potassium hydride; n-Bu₄NI / tetrahydrofuran; various solvent(s) / 50 °C

16.1: 45 percent / OsO₄; N-methylmorpholine N-oxide; buffer / tetrahydrofuran; 2-methyl-propan-2-ol / 96 h / 20 °C / pH 7

17.1: 98 percent / sodium periodate / tetrahydrofuran; H₂O / 48 h

18.1: 25 percent / sodium borohydride / ethanol / 20 °C

19.1: 85 percent / pyridine; DMAP / CH₂Cl₂ / 20 °C

20.1: 53 percent / Oxone; silica gel / CH₂Cl₂ / 2 h / 20 °C

21.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

22.1: 85 percent / DBU / CH₂Cl₂ / 20 °C

23.1: 85 percent / sodium borohydride / ethanol / 4 h / 20 °C

24.1: 90 percent / ethyldiisopropylamine; DMAP / CH₂Cl₂ / 20 °C

With pyridine; B-Br-9-BBN; dmap; Oxone; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 4 A molecular sieve; thexylborane; iodine; tert.-butyl lithium; ethylaluminum dichloride; silica gel; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; hydrazine hydrate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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; water; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; 3.1: Stille coupling / 7.1: Dess-Martin oxidation / 9.1: oxy-Cope rearrangement / 13.1: Dess-Martin oxidation / 14.1: ene reaction / 21.1: Dess-Martin oxidation;

DOI:10.1021/jo062068o

upstream raw materials:

(3R,5aS,7S,8S,9S,9aR)-9-((tert-butyldiphenylsilyloxy)methyl)-3-hydroxy-5,5,8-trimethyl-2,3,5,5a,6,7,8,9-octahydro-1H-cyclopenta[i]inden-7-yl pivalate

chloromethyl methyl ether

(3aR,6S,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

Downstream raw materials:

2-[(2R,5R,6R,8S,9S,10S)-10-(tert-Butyl-diphenyl-silanyloxymethyl)-8-(2,2-dimethyl-propionyloxy)-2-methoxymethoxy-9-methyl-1-oxo-spiro[4.5]dec-6-yl]-2-methyl-propionic acid

2,2-Dimethyl-propionic acid (3R,3aS,5aR,7S,8S,9S,9aS)-9-(tert-butyl-diphenyl-silanyloxymethyl)-3a-hydroxy-3-methoxymethoxy-5,5,8-trimethyl-decahydro-benzo[c]cyclopenta[b]furan-7-yl ester

2,2-Dimethyl-propionic acid (3R,3aS,6aR,8S,9S,10S,10aS)-10-(tert-butyl-diphenyl-silanyloxymethyl)-3a-hydroxy-3-methoxymethoxy-6,6,9-trimethyl-decahydro-4,5-dioxa-cyclopenta[d]naphthalen-8-yl ester