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

Base Information

• Chemical Name: 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
• CAS No.: 1344673-78-4
• Molecular Formula: C₆₃H₉₂O₇Si₃
• Molecular Weight: 1045.68
• Mol file: 1344673-78-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 16 articles about 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 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: 82.0%

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) → 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 (1344673-78-4)

Guidance literature:

With hydrogen; In tetrahydrofuran; methanol; at 20 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201104447

Reference yield: 82.0%

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) → 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 (1344673-78-4) + C63H92O7Si3 (1344673-91-1)

Guidance literature:

With hydrogen; In tetrahydrofuran; methanol; at 20 ℃; for 3h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.201204119

Reference yield:

tert-butyl{[(1S,2S)-2-(tert-butyldimethylsilyl)oxymethylcyclopent-3-en-1-yl]oxy}diphenylsilane (1344673-88-6) → 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 (1344673-78-4)

Guidance literature:

Multi-step reaction with 5 steps

1: N-Bromosuccinimide; water / acetone / 20 °C / Inert atmosphere

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

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

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

5: hydrogen / tetrahydrofuran; methanol / 20 °C / Inert atmosphere

With N-Bromosuccinimide; Burgess Reagent; triethyl borane; triphenylstannane; water; hydrogen; Dess-Martin periodane; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; benzene;

DOI:10.1002/anie.201104447

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

2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol

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

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

Downstream raw materials:

[(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

(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}-4-tert-butyldiphenylsilyloxy-3-hydroxymethyl-1-methylcyclopentanol

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

Refernces

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