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

Base Information

• Chemical Name: 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
• CAS No.: 923571-09-9
• Molecular Formula: C₃₈H₅₆O₈Si
• Molecular Weight: 668.943
• Mol file: 923571-09-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 38 articles about 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 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: 43.0%

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 (923571-08-8) → 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 (923571-09-9)

Guidance literature:

With dihydrogen peroxide; mercury(II) trifluoroacetate; sodium carbonate; In tetrahydrofuran; water; at 50 - 60 ℃; for 0.5h;

DOI:10.1021/jo062068o

Reference yield:

1,7,7-trimethyl-5-oxobicyclo[2.2.1]heptan-2-yl pivalate (923570-65-4) → 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 (923571-09-9)

Guidance literature:

Multi-step reaction with 26 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: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

16.1: 95 percent / DBU / CH₂Cl₂ / 20 °C

17.1: 205 mg / sodium borohydride / ethanol / 4 h / 20 °C

18.1: 93 percent / ethyldiisopropylamine; DMAP / CH₂Cl₂ / 20 °C

19.1: 79 percent / sodium periodate; ruthenium dioxide / CCl₄; acetonitrile; H₂O / 0.25 h

20.1: 34 percent / NaOH / tetrahydrofuran; H₂O

21.1: 83 percent / imidazole / dimethylformamide / 20 °C

22.1: 47 percent / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

23.1: ozone / CH₂Cl₂; methanol / 0.5 h / -78 °C

23.2: 80 percent / triphenylphosphine / CH₂Cl₂; methanol / cooling

24.1: 81 percent / sodium borohydride / methanol / 1 h / 20 °C

25.1: 34 percent / lead tetraacetate / benzene / 0.17 h / 20 °C

26.1: 43 percent / Na₂CO₃; mercuric trifluoroacetate; H₂O₂ / tetrahydrofuran; H₂O / 0.5 h / 50 - 60 °C

With pyridine; 1H-imidazole; B-Br-9-BBN; lead(IV) acetate; dmap; ruthenium(IV) oxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; 4 A molecular sieve; thexylborane; dihydrogen peroxide; iodine; tert.-butyl lithium; mercury(II) trifluoroacetate; ethylaluminum dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium carbonate; Dess-Martin periodane; ozone; hydrazine hydrate; 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; methanol; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; pentane; benzene; 3.1: Stille coupling / 7.1: Dess-Martin oxidation / 9.1: oxy-Cope rearrangement / 13.1: Dess-Martin oxidation / 14.1: ene reaction / 15.1: Dess-Martin oxidation / 20.1: aldol reaction;

DOI:10.1021/jo062068o

Reference yield:

5-iodo-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-yl pivalate (923570-66-5) → 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 (923571-09-9)

Guidance literature:

Multi-step reaction with 24 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: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

14.1: 95 percent / DBU / CH₂Cl₂ / 20 °C

15.1: 205 mg / sodium borohydride / ethanol / 4 h / 20 °C

16.1: 93 percent / ethyldiisopropylamine; DMAP / CH₂Cl₂ / 20 °C

17.1: 79 percent / sodium periodate; ruthenium dioxide / CCl₄; acetonitrile; H₂O / 0.25 h

18.1: 34 percent / NaOH / tetrahydrofuran; H₂O

19.1: 83 percent / imidazole / dimethylformamide / 20 °C

20.1: 47 percent / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

21.1: ozone / CH₂Cl₂; methanol / 0.5 h / -78 °C

21.2: 80 percent / triphenylphosphine / CH₂Cl₂; methanol / cooling

22.1: 81 percent / sodium borohydride / methanol / 1 h / 20 °C

23.1: 34 percent / lead tetraacetate / benzene / 0.17 h / 20 °C

24.1: 43 percent / Na₂CO₃; mercuric trifluoroacetate; H₂O₂ / tetrahydrofuran; H₂O / 0.5 h / 50 - 60 °C

With pyridine; 1H-imidazole; B-Br-9-BBN; lead(IV) acetate; dmap; ruthenium(IV) oxide; sodium hydroxide; sodium tetrahydroborate; sodium periodate; 4 A molecular sieve; thexylborane; dihydrogen peroxide; tert.-butyl lithium; mercury(II) trifluoroacetate; ethylaluminum dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium carbonate; Dess-Martin periodane; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; pentane; benzene; 1.1: Stille coupling / 5.1: Dess-Martin oxidation / 7.1: oxy-Cope rearrangement / 11.1: Dess-Martin oxidation / 12.1: ene reaction / 13.1: Dess-Martin oxidation / 18.1: aldol reaction;

DOI:10.1021/jo062068o

upstream 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

(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

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

Downstream raw materials:

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