{2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl ester

Base Information

Chemical Name:{2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl ester
CAS No.:911393-00-5
Molecular Formula:C₄₈H₇₁NO₇Si₂
Molecular Weight:830.265
Hs Code.:

{2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3<i>H</i>-cyclopenta[<i>a</i>]naphthalen-3-yl}-acetic acid <i>tert</i>-butyl ester

Synonyms:{2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl ester

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Chemical Property of {2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl ester

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Technology Process of {2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl ester

There total 11 articles about {2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl 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: 84.0%

: 911392-92-2
(3'S,3a'S,9b'S,1''S,2''S,4'''S)-2-{2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-hydroxy-2-methyl-3-oxo-propyl]-7-triisopropylsilyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl ester

: 69739-34-0
t-butyldimethylsiyl triflate

: 911393-00-5
{2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl ester

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 20h;
DOI:10.1002/anie.200601003 DOI:10.1002/chem.200700464

Reference yield:

: 911392-86-4
(1S,5R)-2-[(5-tert-butyldimethylsilyloxymethyl)cyclopent-2-enyl]acetic acid tert-butyl ester

: 911393-00-5
{2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 51 percent / Pd(OAc)2; TBACl; NaOAc / dimethylformamide / 144 h / -25 °C

2: 99 percent / NaHCO₃ / methanol / 7 h / 20 °C

3: 90 percent / [Pd(OAc)CH₂(o-P(o-Tol)2)C₆H₄]2; n-Bu₄NOAc / dimethylformamide; acetonitrile; H₂O / 3.5 h / 130 °C

4: 96 percent / DMAP / CH₂Cl₂ / 0.5 h / 0 °C

5: 95 percent / TsOH*H₂O / methanol / 4 h / 0 °C

6: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 0 °C

7: 89 percent / n-Bu₂BOTf; Et₃N / CH₂Cl₂ / -75 - -25 °C

8: 84 percent / DMAP / CH₂Cl₂ / 20 h / 20 °C

With dmap; palladium diacetate; trans-bis(acetato)bis[2-(di-2-tolylphosphino)benzyl]dipalladium(II); di-n-butylboryl trifluoromethanesulfonate; tetrabutyl-ammonium chloride; sodium acetate; tetrabutylammonium acetate; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Heck reaction / 3: Heck reaction / 6: Dess-Martin oxidation / 7: Evams aldol addition;
DOI:10.1002/anie.200601003

Reference yield:

: 911392-90-0
2-[2-(tert-butyldimethylsilyloxymethyl-7-hydroxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl]acetic acid tert-butyl ester

: 911393-00-5
{2-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3-oxo-propyl]-7-triisopropylsilanyloxy-3a,9b-dihydro-3H-cyclopenta[a]naphthalen-3-yl}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / DMAP / CH₂Cl₂ / 0.5 h / 0 °C

2: 95 percent / TsOH*H₂O / methanol / 4 h / 0 °C

3: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 0 °C

4: 89 percent / n-Bu₂BOTf; Et₃N / CH₂Cl₂ / -75 - -25 °C

5: 84 percent / DMAP / CH₂Cl₂ / 20 h / 20 °C

With dmap; di-n-butylboryl trifluoromethanesulfonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; 3: Dess-Martin oxidation / 4: Evams aldol addition;
DOI:10.1002/anie.200601003