Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl ester

Base Information

Chemical Name:Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl ester
CAS No.:357439-48-6
Molecular Formula:C₃₀H₃₈O₉
Molecular Weight:542.626
Hs Code.:

Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl ester

Synonyms:Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl ester

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Chemical Property of Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl ester

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Technology Process of Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl ester

There total 10 articles about Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl 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: 89.0%

: 108-24-7
acetic anhydride

: 776315-73-2
(2R,3S)-2-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-pent-4-ene-1,3-diol

: 357439-48-6
Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl ester

Guidance literature:: With pyridine; dmap; In dichloromethane; for 3h;
DOI:10.1016/j.tet.2004.07.010

Reference yield:

: 357439-43-1
(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

: 357439-48-6
Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: MeLi / diethyl ether / 0.5 h / -78 °C

1.2: 1.31 g / tetrahydrofuran; diethyl ether / 0.75 h / -100 - -90 °C

2.1: Et₃SiH / acetonitrile / 0.67 h / -40 - -20 °C

2.2: 58 percent / tetrabutylammonium fluoride / tetrahydrofuran / 44 h / 20 °C

3.1: 89 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h

With pyridine; triethylsilane; dmap; methyllithium; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/j.tet.2004.07.010

Reference yield:

: 776315-71-0
C₇₆H₈₉NO₁₀Si₂

: 357439-48-6
Acetic acid (S)-1-[(R)-2-acetoxy-1-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-ethyl]-allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2.5 h / -5 °C

2.1: 1.58 g / (1S)-(+)-10-camphorsulfonic acid; p-anisaldehyde / toluene / 90 °C

3.1: MeLi / diethyl ether / 0.5 h / -78 °C

3.2: 1.31 g / tetrahydrofuran; diethyl ether / 0.75 h / -100 - -90 °C

4.1: Et₃SiH / acetonitrile / 0.67 h / -40 - -20 °C

4.2: 58 percent / tetrabutylammonium fluoride / tetrahydrofuran / 44 h / 20 °C

5.1: 89 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h

With pyridine; triethylsilane; dmap; methyllithium; 4-methoxy-benzaldehyde; (+)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; toluene; acetonitrile;
DOI:10.1016/j.tet.2004.07.010