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

Base Information

• Chemical Name: (4R,6R)-4-Hydroxy-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one
• CAS No.: 247146-39-0
• Molecular Formula: C₃₂H₃₆O₅
• Molecular Weight: 500.635

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

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

Chemical Property:

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Technology Process of (4R,6R)-4-Hydroxy-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,6R)-4-Hydroxy-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 → (4R,6R)-4-Hydroxy-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one (247146-39-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; at 80 ℃;

DOI:10.1002/(SICI)1521-3773(19980918)37:17<2354::AID-ANIE2354>3.0.CO;2-9

Reference yield:

2,2-dimethyl-4,4-diphenyl-but-3-enal (5820-02-0) → (4R,6R)-4-Hydroxy-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one (247146-39-0)

Guidance literature:

Multi-step reaction with 9 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

With 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;

DOI:10.1021/ja990860j

Reference yield:

(S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal (215876-04-3) → (4R,6R)-4-Hydroxy-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one (247146-39-0)

Guidance literature:

Multi-step reaction with 3 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

With titanium(IV) dichlorodiisopropylate; pyridinium p-toluenesulfonate; acetic acid; tetramethylammonium triacetoxyborohydride; In toluene; acetonitrile; benzene; 1.1: complexation / 1.2: Condensation / 2.1: Reduction / 3.1: lactonization;

DOI:10.1021/ja990860j

upstream raw materials:

2,2-dimethyl-4,4-diphenyl-but-3-enal

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

(S)-4,4-Dimethyl-6,6-diphenyl-hex-5-ene-1,3-diol

(S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-en-1-ol

Downstream raw materials:

(R)-4-[(2S,4S,6R)-6-Benzenesulfonyl-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-N-phenyl-butyramide

(R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide

(3R,5S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-10,10-diphenyl-dec-9-enoic acid phenylamide

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