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-methyl-3-trimethylsilyloxycyclopentyl}ethanone

Base Information

Chemical Name: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-methyl-3-trimethylsilyloxycyclopentyl}ethanone
CAS No.:1344673-80-8
Molecular Formula:C₅₈H₈₂O₅Si₃
Molecular Weight:943.543
Hs Code.:

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-methyl-3-trimethylsilyloxycyclopentyl}ethanone

Synonyms: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-methyl-3-trimethylsilyloxycyclopentyl}ethanone

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Chemical Property of 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-methyl-3-trimethylsilyloxycyclopentyl}ethanone

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Technology Process of 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-methyl-3-trimethylsilyloxycyclopentyl}ethanone

There total 20 articles about 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-methyl-3-trimethylsilyloxycyclopentyl}ethanone 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: 100.0%

: 75-77-4
chloro-trimethyl-silane

: 1344673-95-5
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

: 1344673-80-8
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-methyl-3-trimethylsilyloxycyclopentyl}ethanone

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;
DOI:10.1002/anie.201104447

Reference yield:

: 1344673-78-4
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

: 1344673-80-8
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-methyl-3-trimethylsilyloxycyclopentyl}ethanone

Guidance literature:: Multi-step reaction with 8 steps

1.1: diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

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

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere

6.1: diethyl ether / 0 °C / Inert atmosphere

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

8.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With 1H-imidazole; oxalyl dichloride; potassium tert-butylate; pyridinium p-toluenesulfonate; Dess-Martin periodane; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction / 3.2: Wittig reaction;
DOI:10.1002/anie.201104447

Reference yield:

: 1344673-94-4
(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

: 1344673-80-8
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-methyl-3-trimethylsilyloxycyclopentyl}ethanone

Guidance literature:: Multi-step reaction with 5 steps

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

2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere

3: diethyl ether / 0 °C / Inert atmosphere

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

5: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With 1H-imidazole; pyridinium p-toluenesulfonate; Dess-Martin periodane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1002/anie.201104447