(R)-3-{(E)-3-[(1S,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-acryloyl}-4-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (R)-3-{(E)-3-[(1S,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-acryloyl}-4-phenyl-oxazolidin-2-one
• CAS No.: 349648-98-2
• Molecular Formula: C₄₀H₅₁NO₆Si₂
• Molecular Weight: 698.019

Synonyms:(R)-3-{(E)-3-[(1S,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-acryloyl}-4-phenyl-oxazolidin-2-one

Chemical Property of (R)-3-{(E)-3-[(1S,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-acryloyl}-4-phenyl-oxazolidin-2-one

Chemical Property:

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Technology Process of (R)-3-{(E)-3-[(1S,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-acryloyl}-4-phenyl-oxazolidin-2-one

There total 16 articles about (R)-3-{(E)-3-[(1S,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-acryloyl}-4-phenyl-oxazolidin-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:

1S,5R-1-acetoxymethyl-5-hydromethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (349648-91-5) → (R)-3-{(E)-3-[(1S,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-acryloyl}-4-phenyl-oxazolidin-2-one (349648-98-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

2.1: 95 percent / K₂CO₃ / methanol / 8 h / 20 °C

3.1: 97 percent / diisopropylethylamine / acetonitrile / 2 h / Heating

4.1: AIBN / benzene / 24 h / Heating

5.1: 75 percent / NaOMe / methanol

6.1: LiBr; methyllithium / tetrahydrofuran; diethyl ether / 0 - 20 °C

6.2: tetrahydrofuran; diethyl ether / 0.33 h / -78 - 0 °C

7.1: 819 mg / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 71 percent / [o-O-C₆H₄-O]BBr; K₂CO₃ / CH₂Cl₂ / 0.5 h / -78 °C

9.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

10.1: 1.19 g / CH₂Cl₂ / 48 h / Heating

With pyridine; 1H-imidazole; oxalyl dichloride; bromocatecholborane; methyllithium; sodium methylate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; benzene; 10.1: Swern oxidation / 11.1: Wittig reaction;

DOI:10.1021/ja010643u

Reference yield:

(1R*,5S*)-1,5-bis(hydroxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one → (R)-3-{(E)-3-[(1S,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-acryloyl}-4-phenyl-oxazolidin-2-one (349648-98-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 14.5 g / pyridine; DMAP / CH₂Cl₂ / 8 h / 0 °C

2.1: lipase from Candida rugosa / 24 h / 20 °C / pH 7

3.1: 98 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

4.1: 95 percent / K₂CO₃ / methanol / 8 h / 20 °C

5.1: 97 percent / diisopropylethylamine / acetonitrile / 2 h / Heating

6.1: AIBN / benzene / 24 h / Heating

7.1: 75 percent / NaOMe / methanol

8.1: LiBr; methyllithium / tetrahydrofuran; diethyl ether / 0 - 20 °C

8.2: tetrahydrofuran; diethyl ether / 0.33 h / -78 - 0 °C

9.1: 819 mg / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 71 percent / [o-O-C₆H₄-O]BBr; K₂CO₃ / CH₂Cl₂ / 0.5 h / -78 °C

11.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

12.1: 1.19 g / CH₂Cl₂ / 48 h / Heating

With pyridine; 1H-imidazole; dmap; oxalyl dichloride; lipase from Candida rugosa; bromocatecholborane; methyllithium; sodium methylate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; benzene; 12.1: Swern oxidation / 13.1: Wittig reaction;

DOI:10.1021/ja010643u

Reference yield:

2,5-bis((tert-butyldimethylsiloxy)methyl)furan (349648-88-0) → (R)-3-{(E)-3-[(1S,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-acryloyl}-4-phenyl-oxazolidin-2-one (349648-98-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: Et₃N / 2,2,2-trifluoro-ethanol / 66 h / 20 °C

1.2: 43 percent / Zn; NH₄Cl / methanol / 72 h / ultrasonic

2.1: aq. HF / acetonitrile / 0.5 h / 0 °C

3.1: 14.5 g / pyridine; DMAP / CH₂Cl₂ / 8 h / 0 °C

4.1: lipase from Candida rugosa / 24 h / 20 °C / pH 7

5.1: 98 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

6.1: 95 percent / K₂CO₃ / methanol / 8 h / 20 °C

7.1: 97 percent / diisopropylethylamine / acetonitrile / 2 h / Heating

8.1: AIBN / benzene / 24 h / Heating

9.1: 75 percent / NaOMe / methanol

10.1: LiBr; methyllithium / tetrahydrofuran; diethyl ether / 0 - 20 °C

10.2: tetrahydrofuran; diethyl ether / 0.33 h / -78 - 0 °C

11.1: 819 mg / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

12.1: 71 percent / [o-O-C₆H₄-O]BBr; K₂CO₃ / CH₂Cl₂ / 0.5 h / -78 °C

13.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

14.1: 1.19 g / CH₂Cl₂ / 48 h / Heating

With pyridine; 1H-imidazole; dmap; oxalyl dichloride; lipase from Candida rugosa; bromocatecholborane; hydrogen fluoride; methyllithium; sodium methylate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2,2,2-trifluoroethanol; acetonitrile; benzene; 14.1: Swern oxidation / 15.1: Wittig reaction;

DOI:10.1021/ja010643u

upstream raw materials:

(4R)-(4-phenyl-1,3-oxazolidin-2-on-3-yl)carbomethylenetriphenylphosphorane

(1S,2R,5R)-1-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-iodo-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

1S,5R-1-acetoxymethyl-5-hydromethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

2,5-bis((tert-butyldimethylsiloxy)methyl)furan

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