(R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one

Base Information

• Chemical Name: (R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one
• CAS No.: 381665-52-7
• Molecular Formula: C₃₇H₆₂O₆Si₃
• Molecular Weight: 687.152

Synonyms:(R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one

Chemical Property of (R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one

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Technology Process of (R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one

There total 11 articles about (R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-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: 80.0%

t-butyldimethylsiyl triflate (69739-34-0) + (R)-6-[(E)-(3R,4R,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one (381665-43-6) → (R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one (381665-52-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane;

DOI:10.1002/1521-3773(20011001)40:19<3667::AID-ANIE3667>3.0.CO;2-6

Reference yield:

triethylsilyl chloride (994-30-9) → (R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one (381665-52-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: imidazole / dimethylformamide

2.1: 89 percent / n-BuLi / tetrahydrofuran / -40 °C

3.1: PPTS / acetone; H₂O

3.2: 65 percent / MnO₂ / CH₂Cl₂

4.1: 70 percent / bis(trifluoroacetoxyiodobenzene) / methanol; H₂O

5.1: 83 percent / Ph₃CBF₄ / diethyl ether

6.1: 93 percent / (p-Me-C₆H₄-i-Pr)Ru[(R,R)-(-N(Ts)-CHPh-CHPh-NH-)] / propan-2-ol / 36 h

7.1: 80 percent / 2,6-lutidine / CH₂Cl₂

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; trityl tetrafluoroborate; pyridinium p-toluenesulfonate; bis-[(trifluoroacetoxy)iodo]benzene; (1R,2R)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine-RuII-p-cymene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone;

DOI:10.1002/1521-3773(20011001)40:19<3667::AID-ANIE3667>3.0.CO;2-6

Reference yield:

2-<(trimethylsilyl)ethynyl>-1,3-dithiane (76649-03-1) → (R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one (381665-52-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / n-BuLi / tetrahydrofuran / -40 °C

2.1: PPTS / acetone; H₂O

2.2: 65 percent / MnO₂ / CH₂Cl₂

3.1: 70 percent / bis(trifluoroacetoxyiodobenzene) / methanol; H₂O

4.1: 83 percent / Ph₃CBF₄ / diethyl ether

5.1: 93 percent / (p-Me-C₆H₄-i-Pr)Ru[(R,R)-(-N(Ts)-CHPh-CHPh-NH-)] / propan-2-ol / 36 h

6.1: 80 percent / 2,6-lutidine / CH₂Cl₂

With 2,6-dimethylpyridine; n-butyllithium; trityl tetrafluoroborate; pyridinium p-toluenesulfonate; bis-[(trifluoroacetoxy)iodo]benzene; (1R,2R)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine-RuII-p-cymene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; acetone;

DOI:10.1002/1521-3773(20011001)40:19<3667::AID-ANIE3667>3.0.CO;2-6

upstream raw materials:

t-butyldimethylsiyl triflate

(R)-6-[(E)-(3R,4R,6R)-6-Hydroxy-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-8-trimethylsilanyl-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one

triethylsilyl chloride

2-<(trimethylsilyl)ethynyl>-1,3-dithiane

Downstream raw materials:

(6R)-6-{(1E,3R,4R,6R,7Z,9Z,11E)-6-{[tert-butyl(dimethyl)silyl]oxy}-13-{[tert-butyl(diphenyl)silyl]oxy}-4-hydroxy-3-methyl-3-[(triethylsilyl)oxy]trideca-1,7,9,11-tetraen-1-yl}-5,6-dihydro-2H-pyran-2-one

(R)-6-[(E)-(3R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-iodo-4-(4-methoxy-benzyloxy)-3-methyl-3-triethylsilanyloxy-oct-1-en-7-ynyl]-5,6-dihydro-pyran-2-one

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