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

Base Information

• Chemical Name: 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
• CAS No.: 923571-08-8
• Molecular Formula: C₃₉H₅₆O₈Si
• Molecular Weight: 680.954

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 37 articles about 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 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: 70.0%

(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) → 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)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In tetrachloromethane; water; acetonitrile; for 0.25h;

DOI:10.1021/jo062068o

Reference yield: 35.0%

(3R,3aS,4R,5R,6aS,8S,9S,10S,10aR)-10-((tert-butyldiphenylsilyloxy)methyl)-3a,4,5-trihydroxy-3-(methoxymethoxy)-6,6,9-trimethyldodecahydrocyclopenta[j]naphthalen-8-yl pivalate (923571-06-6) → 2,2-Dimethyl-propionic acid (2R,5R,6S,7S,8S,10S)-6-(tert-butyl-diphenyl-silanyloxymethyl)-10-(1,1-dimethyl-2-oxo-ethyl)-2-methoxymethoxy-7-methyl-1-oxo-spiro[4.5]dec-8-yl ester + 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)

Guidance literature:

With lead(IV) acetate; In benzene; at 20 ℃; for 0.166667h;

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-[(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)

Guidance literature:

Multi-step reaction with 23 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

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; tert.-butyl lithium; ethylaluminum dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; 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:

(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

(3R,3aS,4R,5R,6aS,8S,9S,10S,10aR)-10-((tert-butyldiphenylsilyloxy)methyl)-3a,4,5-trihydroxy-3-(methoxymethoxy)-6,6,9-trimethyldodecahydrocyclopenta[j]naphthalen-8-yl pivalate

(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:

2,2-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

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