(4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

Base Information

Chemical Name:(4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one
CAS No.:215876-07-6
Molecular Formula:C₃₈H₅₀O₅Si
Molecular Weight:614.897
Hs Code.:

Synonyms:(4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

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Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

There total 9 articles about (4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one 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:

: (S)-3,5-Dihydroxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-10,10-diphenyl-dec-9-enoic acid methyl ester

: 215876-07-6
(4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: PPTS / benzene / 80 °C

2: 64 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

With 2,6-dimethylpyridine; pyridinium p-toluenesulfonate; In dichloromethane; benzene; 1: lactonization / 2: silylation;
DOI:10.1021/ja990860j

Reference yield:

: 5820-02-0
2,2-dimethyl-4,4-diphenyl-but-3-enal

: 215876-07-6
(4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 20 h / -78 - 0 °C

2.1: Zn; AcOH / tetrahydrofuran

3.1: 67 percent / LiBH₄ / methanol; tetrahydrofuran / 0 °C

4.1: PPTS / CH₂Cl₂

5.1: 94 percent / DIBAL-H / CH₂Cl₂ / 0 °C

6.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7.1: TiCl₂(O-iPr)2 / toluene / -78 °C

7.2: 83 percent / toluene / -78 °C

8.1: Me₄NHB(OAc)3; AcOH / acetonitrile / -35 °C

9.1: PPTS / benzene / 80 °C

10.1: 64 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

With 2,6-dimethylpyridine; lithium borohydride; titanium(IV) dichlorodiisopropylate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; zinc; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; benzene; 1.1: Condensation / 2.1: Dehalogenation / 3.1: Reduction / 4.1: acetalization / 5.1: reductive cleavage / 6.1: Oxidation / 7.1: complexation / 7.2: Condensation / 8.1: Reduction / 9.1: lactonization / 10.1: silylation;
DOI:10.1021/ja990860j

Reference yield:

: 215876-04-3
(S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal

: 215876-07-6
(4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: TiCl₂(O-iPr)2 / toluene / -78 °C

1.2: 83 percent / toluene / -78 °C

2.1: Me₄NHB(OAc)3; AcOH / acetonitrile / -35 °C

3.1: PPTS / benzene / 80 °C

4.1: 64 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

With 2,6-dimethylpyridine; titanium(IV) dichlorodiisopropylate; pyridinium p-toluenesulfonate; acetic acid; tetramethylammonium triacetoxyborohydride; In dichloromethane; toluene; acetonitrile; benzene; 1.1: complexation / 1.2: Condensation / 2.1: Reduction / 3.1: lactonization / 4.1: silylation;
DOI:10.1021/ja990860j