[(4R,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-methoxymethoxy-octyl]-phosphonic acid diethyl ester

Base Information

Chemical Name:[(4R,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-methoxymethoxy-octyl]-phosphonic acid diethyl ester
CAS No.:850416-21-6
Molecular Formula:C₂₇H₅₁O₈PSi
Molecular Weight:562.756
Hs Code.:

Synonyms:[(4R,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-methoxymethoxy-octyl]-phosphonic acid diethyl ester

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Chemical Property of [(4R,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-methoxymethoxy-octyl]-phosphonic acid diethyl ester

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Technology Process of [(4R,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-methoxymethoxy-octyl]-phosphonic acid diethyl ester

There total 7 articles about [(4R,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-methoxymethoxy-octyl]-phosphonic acid diethyl ester 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: 87.0%

: 683-08-9
Diethyl methylphosphonate

: 850416-13-6
(3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal

: 850416-21-6
[(4R,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-methoxymethoxy-octyl]-phosphonic acid diethyl ester

Guidance literature:: Diethyl methylphosphonate; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

(3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal; In tetrahydrofuran; at -78 ℃; for 0.416667h;
DOI:10.1055/s-2005-862351

Reference yield:

: 64714-79-0
5-benzyloxy-3-oxo-pentanoic acid ethyl ester

: 850416-21-6
[(4R,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-methoxymethoxy-octyl]-phosphonic acid diethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 82 percent / H₂ / {Ru[(S)-SYNPHOS]Br₂} / ethanol / 14 h / 80 °C / 8250.66 Torr

2.1: 86 percent / P₂O₅ / CHCl₃ / 0.25 h / 0 °C

3.1: LDA / tetrahydrofuran / -40 °C

3.2: 84 percent / tetrahydrofuran / 4.5 h / -40 °C

4.1: 93 percent / H₂ / Ikariya-Mashima's catalyst / methanol / 8 h / 20 °C / 60004.8 Torr

5.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -30 °C

6.1: 85 percent / DIBALH / toluene / 0.42 h / -78 °C

7.1: n-BuLi / tetrahydrofuran / -78 °C

7.2: 87 percent / tetrahydrofuran / 0.42 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; hydrogen; phosphorus pentoxide; diisobutylaluminium hydride; lithium diisopropyl amide; RuBr₂[(S)-(C₆H₂OCH₂CH₂OP(C₆H₅)2)2]; Ikariya-Mashima's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; toluene;
DOI:10.1055/s-2005-862351

Reference yield:

: 95112-81-5,113335-04-9
(S)-ethyl 5-benzyloxy-3-hydroxypentanoate

: 850416-21-6
[(4R,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-methoxymethoxy-octyl]-phosphonic acid diethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / P₂O₅ / CHCl₃ / 0.25 h / 0 °C

2.1: LDA / tetrahydrofuran / -40 °C

2.2: 84 percent / tetrahydrofuran / 4.5 h / -40 °C

3.1: 93 percent / H₂ / Ikariya-Mashima's catalyst / methanol / 8 h / 20 °C / 60004.8 Torr

4.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -30 °C

5.1: 85 percent / DIBALH / toluene / 0.42 h / -78 °C

6.1: n-BuLi / tetrahydrofuran / -78 °C

6.2: 87 percent / tetrahydrofuran / 0.42 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; hydrogen; phosphorus pentoxide; diisobutylaluminium hydride; lithium diisopropyl amide; Ikariya-Mashima's catalyst; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene;
DOI:10.1055/s-2005-862351