(2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal

Base Information

Chemical Name:(2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal
CAS No.:500564-92-1
Molecular Formula:C₃₀H₄₆O₅Si₂
Molecular Weight:542.863
Hs Code.:

Synonyms:(2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal

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Chemical Property of (2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal

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Technology Process of (2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal

There total 6 articles about (2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal 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:

: 500564-86-3
ethyl (2E,4R,5S,6S)-4-(tert-butyldimethylsilyl)-oxy-7-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylene-dioxy)-2-heptenoate

: 500564-92-1
(2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal

Guidance literature:: ethyl (2E,4R,5S,6S)-4-(tert-butyldimethylsilyl)-oxy-7-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylene-dioxy)-2-heptenoate; With ozone; In dichloromethane; at -78 ℃; for 0.25h;

With dimethylsulfide; In dichloromethane; at 20 ℃; for 10h;
DOI:10.1016/S0040-4020(02)01380-7

Reference yield:

: 26685-74-5
1-O-benzyl-3,4-O-isopropylidene-β-L-ribopyranose

: 500564-92-1
(2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / imidazole / dimethylformamide / 16 h / 0 °C

2.1: 83 percent / hydrogen / Pd(OH)2 / ethanol / 48 h

3.1: 98 percent / benzene / 32 h / Heating

4.1: 95 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

5.1: ozone / CH₂Cl₂ / 0.25 h / -78 °C

5.2: Me₂S / CH₂Cl₂ / 10 h / 20 °C

With 1H-imidazole; hydrogen; ozone; palladium dihydroxide; In ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 3.1: Wittig reaction;
DOI:10.1016/S0040-4020(02)01380-7

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 500564-92-1
(2S,3S,4S)-2-(tert-butyldimethylsilyl)oxy-5-(tert-butyldiphenylsilyl)oxy-3,4-(dimethylmethylene)dioxypentanal

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / imidazole / dimethylformamide / 16 h / 0 °C

2.1: 83 percent / hydrogen / Pd(OH)2 / ethanol / 48 h

3.1: 98 percent / benzene / 32 h / Heating

4.1: 95 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

5.1: ozone / CH₂Cl₂ / 0.25 h / -78 °C

5.2: Me₂S / CH₂Cl₂ / 10 h / 20 °C

With 1H-imidazole; hydrogen; ozone; palladium dihydroxide; In ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 3.1: Wittig reaction;
DOI:10.1016/S0040-4020(02)01380-7