Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Base Information

Chemical Name:Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester
CAS No.:199857-51-7
Molecular Formula:C₃₆H₆₀O₇Si
Molecular Weight:632.954
Hs Code.:

Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Synonyms:Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

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Chemical Property of Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

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Technology Process of Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

There total 22 articles about Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-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:

: 108-24-7
acetic anhydride

: (2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-2-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undecane-4,10-diol

: 199857-51-7
Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 2.5h; Yield given;
DOI:10.1016/S0040-4039(97)10126-5

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 199857-51-7
Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Guidance literature:: Multi-step reaction with 18 steps

1: imidazole, DMAP / CH₂Cl₂ / 1.5 h / 20 °C

2: 1.) MeONHMe*HCl, iPrMgCl / 1.) THF, -20 deg C, 1 h; 2.) THF, 0 deg C to 20 deg C, 2 h

3: Et₃N / diethyl ether / 0.5 h / 0 °C

4: - 78 deg C, 5-6 h then -20 deg C, 16 h

5: 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

6: toluene / 1.5 h / 110 °C

7: PPTS / methanol; CH₂Cl₂ / 0.17 h / 20 °C

8: DEAD, PPh₃ / benzene / 0.33 h / 20 °C

9: 1.) K₂CO₃; 2.) PPh₃ / methanol / 3 h

10: 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

11: DDQ, pH 7 buffer / CH₂Cl₂ / 0.75 h / 0 °C

12: Dess-Martin periodinane / CH₂Cl₂ / 0.42 h / 20 °C

13: 97 percent / 2.) H₂O₂, pH=7 buffer / methanol / 6 h / -78 °C

14: 88 percent / PPTS / methanol; CH₂Cl₂ / 0.67 h / 20 °C

15: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

16: tetrahydrofuran / 3 h / -78 - 20 °C

17: CSA / methanol; CH₂Cl₂ / 1.25 h

18: DMAP / CH₂Cl₂ / 2.5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; pH 7 buffer; pH=7 buffer; camphor-10-sulfonic acid; dihydrogen peroxide; isopropylmagnesium chloride; N,O-dimethylhydroxylamine*hydrochloride; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; benzene;
DOI:10.1016/S0040-4039(97)10126-5

Reference yield:

: 158783-84-7
(S)-methyl 2-methyl-3-(triisopropylsilyloxy)propanoate

: 199857-51-7
Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 1.) MeONHMe*HCl, iPrMgCl / 1.) THF, -20 deg C, 1 h; 2.) THF, 0 deg C to 20 deg C, 2 h

2: Et₃N / diethyl ether / 0.5 h / 0 °C

3: - 78 deg C, 5-6 h then -20 deg C, 16 h

4: 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

5: toluene / 1.5 h / 110 °C

6: PPTS / methanol; CH₂Cl₂ / 0.17 h / 20 °C

7: DEAD, PPh₃ / benzene / 0.33 h / 20 °C

8: 1.) K₂CO₃; 2.) PPh₃ / methanol / 3 h

9: 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

10: DDQ, pH 7 buffer / CH₂Cl₂ / 0.75 h / 0 °C

11: Dess-Martin periodinane / CH₂Cl₂ / 0.42 h / 20 °C

12: 97 percent / 2.) H₂O₂, pH=7 buffer / methanol / 6 h / -78 °C

13: 88 percent / PPTS / methanol; CH₂Cl₂ / 0.67 h / 20 °C

14: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

15: tetrahydrofuran / 3 h / -78 - 20 °C

16: CSA / methanol; CH₂Cl₂ / 1.25 h

17: DMAP / CH₂Cl₂ / 2.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; pH 7 buffer; pH=7 buffer; camphor-10-sulfonic acid; dihydrogen peroxide; isopropylmagnesium chloride; N,O-dimethylhydroxylamine*hydrochloride; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; benzene;
DOI:10.1016/S0040-4039(97)10126-5