(1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitro-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane

Base Information

• Chemical Name: (1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitro-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane
• CAS No.: 267872-94-6
• Molecular Formula: C₃₈H₅₇NO₄Si₂
• Molecular Weight: 648.046

Synonyms:(1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitro-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane

Chemical Property of (1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitro-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitro-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane

There total 27 articles about (1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitro-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane 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: 67.0%

(1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-iodo-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane (267873-02-9) → (1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitro-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane (267872-94-6)

Guidance literature:

With silver(I) nitrite; In diethyl ether; for 48h; Heating;

DOI:10.1016/S0040-4039(99)02103-6

Reference yield:

(1R,2R,6R)-2-Hydroxymethyl-7,7-dimethyl-bicyclo[4.1.0]hept-4-en-3-one (267872-80-0) → (1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitro-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane (267872-94-6)

Guidance literature:

Multi-step reaction with 22 steps

1.1: aq. H₂O₂; NaOH / tetrahydrofuran / 2 h / 0 °C

2.1: pyridine / CH₂Cl₂ / 10 h / 20 °C

3.1: 87 percent / Al-Hg / tetrahydrofuran; aq. ethanol / 96 h / -45 °C

4.1: 60 percent / imidazole / dimethylformamide / 6 h / 20 °C

5.1: 70 percent / s-BuLi; CeCl₃ / tetrahydrofuran / 2 h / -40 - 0 °C

6.1: 73 percent / KH / tetrahydrofuran / 2 h / 20 °C

7.1: CH₂Cl₂ / 3 h / 0 °C

7.2: 70 percent / NaBH₄ / 0.17 h / 0 °C

8.1: p-TsOH / acetone; H₂O / 10 h / 20 °C

9.1: N-BuLi / tetrahydrofuran / 2 h / 0 °C

10.1: 88 percent / n-Bu₄NF / tetrahydrofuran / 11 h / 20 °C

11.1: 86 percent / SO₃*pyridine; NEt₃ / dimethylsulfoxide / 1 h / 20 °C

12.1: 86 percent / NaBH₄ / methanol / 0.5 h / 0 °C

13.1: 96 percent / imisazole / dimethylformamide / 22 h / 20 °C

14.1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

15.1: SO₃*pyridine; Et₃N / dimethylsulfoxide / 2 h / 20 °C

16.1: 73 percent / KHMDS / tetrahydrofuran / 18 h / 20 °C

17.1: DIBAL-H / toluene / 3 h / -78 °C

18.1: imidazole / dimethylformamide / 5 h / 20 °C

19.1: DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

20.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

21.1: NaI / butan-2-one / 9 h / 50 °C

22.1: 67 percent / AgNO₂ / diethyl ether / 48 h / Heating

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; silver(I) nitrite; n-butyllithium; cerium(III) chloride; pyridine-SO₃ complex; aluminium amalgam; tetrabutyl ammonium fluoride; dihydrogen peroxide; sec.-butyllithium; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; butanone; 1.1: Epoxidation / 2.1: Esterification / 3.1: Reduction / 4.1: silylation / 5.1: Alkylation / 6.1: Hydrolysis / 7.1: oxymercuration / 7.2: Reduction / 8.1: Elimination / 9.1: Alkylation / 10.1: desilylation / 11.1: Oxidation / 12.1: Reduction / 13.1: Acetoxylation / 14.1: Reduction / 15.1: Oxidation / 16.1: Alkylation / 17.1: Reduction / 18.1: Etherification / 19.1: Reduction / 20.1: Esterification / 21.1: Iodination / 22.1: Nitration;

DOI:10.1016/S0040-4039(99)02103-6

Reference yield:

(1R,2R,6R)-2-Hydroxymethyl-7,7-dimethyl-bicyclo[4.1.0]heptan-3-one (267872-79-7) → (1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-nitro-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane (267872-94-6)

Guidance literature:

Multi-step reaction with 26 steps

1.1: 83 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: 84 percent / LDA; zirconocene dichloride / tetrahydrofuran / 2 h / -78 °C

3.1: 85 percent / m-CPBA / CH₂Cl₂ / 2 h / 20 °C

4.1: 100 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C

5.1: aq. H₂O₂; NaOH / tetrahydrofuran / 2 h / 0 °C

6.1: pyridine / CH₂Cl₂ / 10 h / 20 °C

7.1: 87 percent / Al-Hg / tetrahydrofuran; aq. ethanol / 96 h / -45 °C

8.1: 60 percent / imidazole / dimethylformamide / 6 h / 20 °C

9.1: 70 percent / s-BuLi; CeCl₃ / tetrahydrofuran / 2 h / -40 - 0 °C

10.1: 73 percent / KH / tetrahydrofuran / 2 h / 20 °C

11.1: CH₂Cl₂ / 3 h / 0 °C

11.2: 70 percent / NaBH₄ / 0.17 h / 0 °C

12.1: p-TsOH / acetone; H₂O / 10 h / 20 °C

13.1: N-BuLi / tetrahydrofuran / 2 h / 0 °C

14.1: 88 percent / n-Bu₄NF / tetrahydrofuran / 11 h / 20 °C

15.1: 86 percent / SO₃*pyridine; NEt₃ / dimethylsulfoxide / 1 h / 20 °C

16.1: 86 percent / NaBH₄ / methanol / 0.5 h / 0 °C

17.1: 96 percent / imisazole / dimethylformamide / 22 h / 20 °C

18.1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

19.1: SO₃*pyridine; Et₃N / dimethylsulfoxide / 2 h / 20 °C

20.1: 73 percent / KHMDS / tetrahydrofuran / 18 h / 20 °C

21.1: DIBAL-H / toluene / 3 h / -78 °C

22.1: imidazole / dimethylformamide / 5 h / 20 °C

23.1: DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

24.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

25.1: NaI / butan-2-one / 9 h / 50 °C

26.1: 67 percent / AgNO₂ / diethyl ether / 48 h / Heating

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; silver(I) nitrite; n-butyllithium; cerium(III) chloride; pyridine-SO₃ complex; aluminium amalgam; zirconocene dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sec.-butyllithium; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; butanone; 1.1: silylation / 2.1: selenylation / 3.1: Oxidation / 4.1: desilylation / 5.1: Epoxidation / 6.1: Esterification / 7.1: Reduction / 8.1: silylation / 9.1: Alkylation / 10.1: Hydrolysis / 11.1: oxymercuration / 11.2: Reduction / 12.1: Elimination / 13.1: Alkylation / 14.1: desilylation / 15.1: Oxidation / 16.1: Reduction / 17.1: Acetoxylation / 18.1: Reduction / 19.1: Oxidation / 20.1: Alkylation / 21.1: Reduction / 22.1: Etherification / 23.1: Reduction / 24.1: Esterification / 25.1: Iodination;

DOI:10.1016/S0040-4039(99)02103-6

upstream raw materials:

(1S,2S,3R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-iodo-but-1-enyl]-7,7-dimethyl-3-vinyl-bicyclo[4.1.0]heptane

(1R,2R,6R)-2-Hydroxymethyl-7,7-dimethyl-bicyclo[4.1.0]hept-4-en-3-one

(1R,2R,6R)-2-Hydroxymethyl-7,7-dimethyl-bicyclo[4.1.0]heptan-3-one

(1R,2R,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-7,7-dimethyl-bicyclo[4.1.0]hept-4-en-3-one

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