(Z)-(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-en-3-ol

Base Information

Chemical Name:(Z)-(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-en-3-ol
CAS No.:333788-82-2
Molecular Formula:C₃₈H₆₄O₆Si₂
Molecular Weight:673.094
Hs Code.:

Synonyms:(Z)-(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-en-3-ol

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Chemical Property of (Z)-(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-en-3-ol

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Technology Process of (Z)-(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-en-3-ol

There total 13 articles about (Z)-(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-en-3-ol 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: 99.0%

: 333788-71-9
(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-ol

: 333788-82-2
(Z)-(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-en-3-ol

Guidance literature:: With quinoline; hydrogen; Lindlar catalyst; In methanol;
DOI:10.1016/S0040-4039(00)02281-4

Reference yield:

: 84379-53-3
2-O-benzyl-3,4-O-isopropylidene-L-threitol

: 333788-82-2
(Z)-(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-en-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / TEA; DMAP / CH₂Cl₂

2: 93 percent / diethyl ether / -65 - 0 °C

3: 97 percent / PPTS / ethanol / 80 °C

4: 100 percent / TEA; DMAP / CH₂Cl₂ / 60 °C

5: 98 percent / TEA; DMAP / CH₂Cl₂

6: 96 percent / TBAF / tetrahydrofuran

7: 93 percent / EDA / dimethylsulfoxide / 0 °C

8: 98 percent / AgNO₃; pyridine / acetonitrile

9: 78 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

10: 99 percent / H₂; quinoline / Lindlar cat. / methanol

With pyridine; quinoline; diazoacetic acid ethyl ester; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; silver nitrate; Lindlar catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 9: Yamaguchi coupling reaction;
DOI:10.1016/S0040-4039(00)02281-4

Reference yield:

: 131446-96-3
(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

: 333788-82-2
(Z)-(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-en-3-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 93 percent / diethyl ether / -65 - 0 °C

2: 97 percent / PPTS / ethanol / 80 °C

3: 100 percent / TEA; DMAP / CH₂Cl₂ / 60 °C

4: 98 percent / TEA; DMAP / CH₂Cl₂

5: 96 percent / TBAF / tetrahydrofuran

6: 93 percent / EDA / dimethylsulfoxide / 0 °C

7: 98 percent / AgNO₃; pyridine / acetonitrile

8: 78 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

9: 99 percent / H₂; quinoline / Lindlar cat. / methanol

With pyridine; quinoline; diazoacetic acid ethyl ester; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; silver nitrate; Lindlar catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 8: Yamaguchi coupling reaction;
DOI:10.1016/S0040-4039(00)02281-4