(1S,2R,3R,7R,8R,9S,10R)-12-benzyl-2,9-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-8-triethylsilanyloxy-4,6-dioxa-12-aza-tricyclo[8.2.1.0]tridecan-11-one

Base Information

• Chemical Name: (1S,2R,3R,7R,8R,9S,10R)-12-benzyl-2,9-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-8-triethylsilanyloxy-4,6-dioxa-12-aza-tricyclo[8.2.1.0]tridecan-11-one
• CAS No.: 583040-11-3
• Molecular Formula: C₃₇H₆₇NO₆Si₃
• Molecular Weight: 706.199

Synonyms:(1S,2R,3R,7R,8R,9S,10R)-12-benzyl-2,9-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-8-triethylsilanyloxy-4,6-dioxa-12-aza-tricyclo[8.2.1.0]tridecan-11-one

Chemical Property of (1S,2R,3R,7R,8R,9S,10R)-12-benzyl-2,9-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-8-triethylsilanyloxy-4,6-dioxa-12-aza-tricyclo[8.2.1.0]tridecan-11-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,7R,8R,9S,10R)-12-benzyl-2,9-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-8-triethylsilanyloxy-4,6-dioxa-12-aza-tricyclo[8.2.1.0]tridecan-11-one

There total 9 articles about (1S,2R,3R,7R,8R,9S,10R)-12-benzyl-2,9-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-8-triethylsilanyloxy-4,6-dioxa-12-aza-tricyclo[8.2.1.0]tridecan-11-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: 85.0%

t-butyldimethylsiyl triflate (69739-34-0) + (1''R,2S,2'S,4'''S,5'''R)-{5-[(1-benzyl-5-oxo-pyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}triethylsilanyloxyacetaldehyde (583040-10-2) → (1S,2R,3R,7R,8R,9S,10R)-12-benzyl-2,9-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-8-triethylsilanyloxy-4,6-dioxa-12-aza-tricyclo[8.2.1.0]tridecan-11-one (583040-11-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/jo0344539

Reference yield:

N-tert-butoxycarbonyl-6,7;8,9-di-O-isopropylidene-2,3-dideoxy-D-glycero-D-galacto-nonono-1,4-lactam (152611-53-5) → (1S,2R,3R,7R,8R,9S,10R)-12-benzyl-2,9-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-8-triethylsilanyloxy-4,6-dioxa-12-aza-tricyclo[8.2.1.0]tridecan-11-one (583040-11-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 2,6-lutidine / CH₂Cl₂ / Heating

2: ceric ammonium nitrate / acetonitrile / 2 h / Heating

3: KH / tetrahydrofuran; various solvent(s) / 6 h / 60 °C

4: 2.39 g / acetic acid / H₂O / 8 h / 50 °C

5: 85 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C

6: 95 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / -80 - 25 °C

7: 85 percent / diisopropylethylamine / CH₂Cl₂ / 2 h / 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; oxalyl dichloride; ammonium cerium(IV) nitrate; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile; 6: Swern oxidation;

DOI:10.1021/jo0344539

Reference yield:

(1'R,2S,4''R,5''R,5'''R)-2-[hydroxy-(2,2,2',2'-tetramethyl-[4,4']bis[[1,3]dioxolanyl]-5-yl)methyl]-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester (152611-51-3) → (1S,2R,3R,7R,8R,9S,10R)-12-benzyl-2,9-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-8-triethylsilanyloxy-4,6-dioxa-12-aza-tricyclo[8.2.1.0]tridecan-11-one (583040-11-3)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH₄; NiCl₂ / methanol / 40 h / 0 °C

2: 2,6-lutidine / CH₂Cl₂ / Heating

3: ceric ammonium nitrate / acetonitrile / 2 h / Heating

4: KH / tetrahydrofuran; various solvent(s) / 6 h / 60 °C

5: 2.39 g / acetic acid / H₂O / 8 h / 50 °C

6: 85 percent / 4-dimethylaminopyridine; pyridine / 6 h / 20 °C

7: 95 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / -80 - 25 °C

8: 85 percent / diisopropylethylamine / CH₂Cl₂ / 2 h / 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; ammonium cerium(IV) nitrate; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 7: Swern oxidation;

DOI:10.1021/jo0344539

upstream raw materials:

t-butyldimethylsiyl triflate

(1''R,2S,2'S,4'''S,5'''R)-{5-[(1-benzyl-5-oxo-pyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}triethylsilanyloxyacetaldehyde

N-tert-butoxycarbonyl-6,7;8,9-di-O-isopropylidene-2,3-dideoxy-D-glycero-D-galacto-nonono-1,4-lactam

(1'R,2S,4''R,5''R,5'''R)-2-[hydroxy-(2,2,2',2'-tetramethyl-[4,4']bis[[1,3]dioxolanyl]-5-yl)methyl]-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

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