2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate

Base Information

• Chemical Name: 2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate
• CAS No.: 1344673-74-0
• Molecular Formula: C₆₃H₉₀O₇Si₃
• Molecular Weight: 1043.66
• Mol file: 1344673-74-0.mol

Synonyms:2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate

Chemical Property of 2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate

There total 36 articles about 2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate 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: 92.0%

2-[(2R,4S,5S,6R,7S)-7-[(R)-((1S,2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentyl)(hydroxy)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate (1344673-77-3) → 2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate (1344673-74-0)

Guidance literature:

With Burgess Reagent; In benzene; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201104447

Reference yield:

(-)-tert-butyl-[(2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-vinyl-1-oxaspiro[4.4]non-2-ylmethoxy]diphenylsilane (890027-31-3) → 2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate (1344673-74-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: pyridine; dmap / dichloromethane / 20 °C / Inert atmosphere

3.1: dimethylsulfide; boron trifluoride diethyl etherate / dichloromethane / -30 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

5.1: triethyl borane; triphenylstannane / hexane; benzene / 20 °C / Inert atmosphere

6.1: Burgess Reagent / benzene / 20 °C / Inert atmosphere

With pyridine; dmap; Burgess Reagent; dimethylsulfide; triethyl borane; boron trifluoride diethyl etherate; triphenylstannane; Dess-Martin periodane; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; hexane; dichloromethane; benzene; 1.1: Hydroboration reaction;

DOI:10.1002/anie.201104447

Reference yield:

2-methyl-2-(3-phenyl-2-propenyl)malonic acid monomethyl ester (1444378-51-1) → 2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate (1344673-74-0)

Guidance literature:

Multi-step reaction with 24 steps

1.1: pig liver esterase / 168 h / 30 °C / pH 8 / Enzymatic reaction

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate; methanol / tetrahydrofuran / -30 - 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine; sodium iodide / dichloromethane / Reflux; Inert atmosphere

5.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C / Inert atmosphere

6.1: dmap; pyridine / dichloromethane / 20 °C

7.1: ozone / methanol / -78 °C / Inert atmosphere

7.2: -78 - 0 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / dichloromethane / 20 °C / Inert atmosphere

9.1: methanol; potassium carbonate / 20 °C / Inert atmosphere

10.1: triethylamine; dimethyl sulfoxide; sulfur trioxide pyridine complex / dichloromethane / 0 °C / Inert atmosphere

11.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

11.2: -78 - 20 °C / Inert atmosphere

12.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C / Inert atmosphere

13.1: methanesulfonyl chloride; lithium chloride; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

14.1: methyllithium / diethyl ether; N,N,N,N,N,N-hexamethylphosphoric triamide / 0.05 h / 0 °C / Inert atmosphere

14.2: -60 °C / Inert atmosphere

15.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

16.1: 1H-imidazole; triphenylphosphine; iodine / benzene / 20 °C / Inert atmosphere

17.1: tert.-butyl lithium / diethyl ether; pentane / 0.25 h / -78 °C / Inert atmosphere

17.2: -78 °C / Inert atmosphere

18.1: boron trifluoride diethyl etherate / diethyl ether; toluene / 12 h / -60 °C / Inert atmosphere

19.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

19.2: 3 h / 20 °C

20.1: dmap; pyridine / dichloromethane / 20 °C / Inert atmosphere

21.1: boron trifluoride diethyl etherate; dimethylsulfide / dichloromethane / 3 h / -30 °C

22.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

23.1: triphenylstannane; triethyl borane / benzene; hexane / 20 °C / Inert atmosphere

24.1: Burgess Reagent / benzene / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; pig liver esterase; oxalyl dichloride; Burgess Reagent; dimethylsulfide; triethyl borane; boron trifluoride diethyl etherate; triphenylstannane; potassium tert-butylate; methyllithium; iodine; tert.-butyl lithium; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; sodium iodide; lithium chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; benzene; 10.1: |Parikh-Doering Oxidation / 11.2: |Horner-Wadsworth-Emmons Olefination / 18.1: |Hosomi-Sakurai Reaction / 22.1: |Dess-Martin Oxidation;

DOI:10.1002/chem.201204119

upstream raw materials:

(-)-tert-butyl-[(2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-vinyl-1-oxaspiro[4.4]non-2-ylmethoxy]diphenylsilane

(2R,3S,4S)-2-bromo-3-(tert-butyldimethylsilyl)oxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

(2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

2-[(2R,4S,5S,6R,7S)-7-[(R)-((1S,2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentyl)(hydroxy)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate

Downstream raw materials:

2-[(2R,4S,5S,6R,7R)-7-[((1S,2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentyl)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate

(1R,2S,3S,4S)-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxy-2-{[(2R,4S,5S,6R,7R)-2-tert-butyldiphenylsilyloxymethyl-6-(2-hydroxyethyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-1-methylcyclopentanol

[(2R,4S,5S,6R,7R)-7-[((1S,2R,4S,5S)-5-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxy-2-hydroxy-2-methylcyclopentyl)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]acetaldehyde

(1R,2S,3S,4S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxy-1-methylcyclopentanol

Refernces

• 1、 Tsuna, Kazuhiro,Noguchi, Naoyoshi,Nakada, Masahisa. "Convergent total synthesis of (+)-ophiobolin A". . p. 9452 - 9455. Retrieved 2011/11/06.