(1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate

Base Information

• Chemical Name: (1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate
• CAS No.: 851791-29-2
• Molecular Formula: C₃₃H₄₇ClO₆Si
• Molecular Weight: 603.271
• Mol file: 851791-29-2.mol

Synonyms:(1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate

Chemical Property of (1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate

There total 15 articles about (1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate 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: 91.0%

(1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-hydroxy-2-methyl-3-vinylcyclohexyl benzoate (851791-28-1) + chloromethyl methyl ether (107-30-2) → (1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate (851791-29-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 120h;

DOI:10.1021/jo050039s

Reference yield:

(1S,5S,8S)-8-methyl-8-vinyl-6-oxabicyclo[3.2.1]octane-2,7-dione → (1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate (851791-29-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: potassium tert-butoxide / toluene / 3 h / Heating

1.2: 2.06 g / toluene / 2 h / 20 °C

2.1: 85 percent / selenium dioxide; tert-butyl hydroperoxide; salicylic acid / CH₂Cl₂; H₂O / 72 h / Heating

3.1: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C

4.1: 80 percent / OsO₄; sodium metaperiodate / tetrahydrofuran; H₂O / 6 h / 20 °C

5.1: 90 percent / NaBH₄ / methanol / 0.5 h / -78 - 0 °C

6.1: 75 percent / m-CPBA / CH₂Cl₂; H₂O / 120 h / 37 °C

7.1: 88 percent / NaH; Bu₄NI / tetrahydrofuran / 12 h / 20 °C

8.1: diisobutylaluminum hydride / toluene / 0.33 h / -80 °C

9.1: 592 mg / pyridine / benzene; tetrahydrofuran / -78 - 20 °C

10.1: 86 percent / pyridine / 12 h / 20 °C

11.1: 78 percent / Et₂AlCl / CH₂Cl₂; hexane / -78 - 20 °C

12.1: 91 percent / diisopropylethylamine / CH₂Cl₂ / 120 h / 20 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; selenium(IV) oxide; potassium tert-butylate; diethylaluminium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; salicylic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 1.2: Wittig olefination / 9.1: Tebbe olefination;

DOI:10.1021/jo050039s

Reference yield:

(1R,5S,8S)-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one (1039740-17-4) → (1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate (851791-29-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / selenium dioxide; tert-butyl hydroperoxide; salicylic acid / CH₂Cl₂; H₂O / 72 h / Heating

2: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C

3: 80 percent / OsO₄; sodium metaperiodate / tetrahydrofuran; H₂O / 6 h / 20 °C

4: 90 percent / NaBH₄ / methanol / 0.5 h / -78 - 0 °C

5: 75 percent / m-CPBA / CH₂Cl₂; H₂O / 120 h / 37 °C

6: 88 percent / NaH; Bu₄NI / tetrahydrofuran / 12 h / 20 °C

7: diisobutylaluminum hydride / toluene / 0.33 h / -80 °C

8: 592 mg / pyridine / benzene; tetrahydrofuran / -78 - 20 °C

9: 86 percent / pyridine / 12 h / 20 °C

10: 78 percent / Et₂AlCl / CH₂Cl₂; hexane / -78 - 20 °C

11: 91 percent / diisopropylethylamine / CH₂Cl₂ / 120 h / 20 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; selenium(IV) oxide; diethylaluminium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; salicylic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 8: Tebbe olefination;

DOI:10.1021/jo050039s

upstream raw materials:

(1S,2R,3S,4R,5R)-2-benzyloxymethyl-5-(tert-butyldimethylsilyloxy)-4-chloromethyl-4-hydroxy-2-methyl-3-vinylcyclohexyl benzoate

chloromethyl methyl ether

(1R,5S,8S)-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one

(1R,3R,5S,8S)-3-hydroxy-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one

Downstream raw materials:

{(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane

(1S,2R,3S,4R,5R)-2-benzyloxymethyl-4-chloromethyl-5-hydroxy-4-methoxymethoxy-2-methyl-3-vinyl-cyclohexyl benzoate