(2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol

Base Information

• Chemical Name: (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol
• CAS No.: 199857-49-3
• Molecular Formula: C₃₉H₇₀O₆Si₂
• Molecular Weight: 691.152
• Mol file: 199857-49-3.mol

Synonyms:(2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol

Chemical Property of (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol

There total 27 articles about (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-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: 88.0%

(3S,5S,9S,11S)-1-benzyloxy-5-(t-butyldimethylsiloxy)-9-hydroxy-13-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-3,11-bis(triethylsiloxy)-tetradec-13-en-7-one (199857-48-2) → (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol (199857-49-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; dichloromethane; at 20 ℃; for 0.666667h;

DOI:10.1016/S0040-4039(97)10126-5 DOI:10.1039/b504146e

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol (199857-49-3)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 99 percent / imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

2.1: 99.5 g / i-PrMgCl / tetrahydrofuran / 1 h / -20 °C

3.1: 75 percent / tetrahydrofuran; diethyl ether / 3 h / 0 °C

4.1: Et₃N / diethyl ether / -78 - 0 °C

5.1: diethyl ether / 21 h / -78 - -20 °C

5.2: 4.08 g / aq. H₂O₂ / methanol / 2.5 h / 20 °C

6.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

7.1: Zn; PbI₂; TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 4.5 h / 20 °C

8.1: 5.64 g / PPTS / methanol; CH₂Cl₂ / 0.5 h / 20 °C

9.1: 94 percent / Ph₃P; DEAD / benzene / 0.33 h / 20 °C

10.1: 97 percent / K₂CO₃ / methanol / 16 h / 20 °C

11.1: 97 percent / imidazole / dimethylformamide / 16 h / 20 °C

12.1: 95 percent / DDQ / CH₂Cl₂ / 0.75 h / 0 °C / pH 7

13.1: 91 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

14.1: diethyl ether / 19 h / -78 - -20 °C

14.2: 100 percent / aq. H₂O₂ / methanol / 2.5 h / 20 °C

15.1: 88 percent / PPTS / methanol; CH₂Cl₂ / 0.67 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lead(II) iodide; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 9.1: Mitsunobu inversion;

DOI:10.1039/b504146e

Reference yield:

(S)-methyl 2-methyl-3-(triisopropylsilyloxy)propanoate (158783-84-7) → (2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol (199857-49-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 99.5 g / i-PrMgCl / tetrahydrofuran / 1 h / -20 °C

2.1: 75 percent / tetrahydrofuran; diethyl ether / 3 h / 0 °C

3.1: Et₃N / diethyl ether / -78 - 0 °C

4.1: diethyl ether / 21 h / -78 - -20 °C

4.2: 4.08 g / aq. H₂O₂ / methanol / 2.5 h / 20 °C

5.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

6.1: Zn; PbI₂; TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 4.5 h / 20 °C

7.1: 5.64 g / PPTS / methanol; CH₂Cl₂ / 0.5 h / 20 °C

8.1: 94 percent / Ph₃P; DEAD / benzene / 0.33 h / 20 °C

9.1: 97 percent / K₂CO₃ / methanol / 16 h / 20 °C

10.1: 97 percent / imidazole / dimethylformamide / 16 h / 20 °C

11.1: 95 percent / DDQ / CH₂Cl₂ / 0.75 h / 0 °C / pH 7

12.1: 91 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

13.1: diethyl ether / 19 h / -78 - -20 °C

13.2: 100 percent / aq. H₂O₂ / methanol / 2.5 h / 20 °C

14.1: 88 percent / PPTS / methanol; CH₂Cl₂ / 0.67 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lead(II) iodide; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 8.1: Mitsunobu inversion;

DOI:10.1039/b504146e

upstream raw materials:

(3S,5S,9S,11S)-1-benzyloxy-5-(t-butyldimethylsiloxy)-9-hydroxy-13-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-3,11-bis(triethylsiloxy)-tetradec-13-en-7-one

triisopropylsilyl chloride

(R)-1-benzyloxy-hex-5-en-3-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-4-methyl-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol

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

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

(2S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undecan-4-one