[(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

Base Information Edit

Chemical Name:[(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
CAS No.:1344673-93-3
Molecular Formula:C₅₉H₈₆O₆Si₃
Molecular Weight:975.585
Hs Code.:
Mol file:1344673-93-3.mol

[(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

Synonyms:[(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

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Chemical Property of [(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 Edit

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Technology Process of [(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

There total 17 articles about [(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 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: 98.0%

: 1344673-92-2
(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

: 1344673-93-3
[(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

Guidance literature:: (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; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 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

: 1344673-93-3
[(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

Guidance literature:: Multi-step reaction with 2 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

With oxalyl dichloride; dimethyl sulfoxide; In diethyl ether; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1002/anie.201104447

Reference yield:

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

: 1344673-93-3
[(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

Guidance literature:: Multi-step reaction with 7 steps

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

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

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

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

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

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

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

7.2: -78 - 20 °C / Inert atmosphere

With N-Bromosuccinimide; oxalyl dichloride; Burgess Reagent; triethyl borane; triphenylstannane; water; hydrogen; Dess-Martin periodane; dimethyl sulfoxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; benzene; 7.1: Swern oxidation / 7.2: Swern oxidation;
DOI:10.1002/anie.201104447