(1R,2S,3R,7R,8R,9S)-10-benzyl-2,8-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-4,6-dioxa-10-aza-tricyclo[7.2.1.0]dodecan-11-one

Base Information

Chemical Name:(1R,2S,3R,7R,8R,9S)-10-benzyl-2,8-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-4,6-dioxa-10-aza-tricyclo[7.2.1.0]dodecan-11-one
CAS No.:583040-06-6
Molecular Formula:C₃₀H₅₁NO₅Si₂
Molecular Weight:561.91
Hs Code.:

Synonyms:(1R,2S,3R,7R,8R,9S)-10-benzyl-2,8-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-4,6-dioxa-10-aza-tricyclo[7.2.1.0]dodecan-11-one

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Chemical Property of (1R,2S,3R,7R,8R,9S)-10-benzyl-2,8-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-4,6-dioxa-10-aza-tricyclo[7.2.1.0]dodecan-11-one

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Technology Process of (1R,2S,3R,7R,8R,9S)-10-benzyl-2,8-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-4,6-dioxa-10-aza-tricyclo[7.2.1.0]dodecan-11-one

There total 8 articles about (1R,2S,3R,7R,8R,9S)-10-benzyl-2,8-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-4,6-dioxa-10-aza-tricyclo[7.2.1.0]dodecan-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: 80.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 583040-05-5
(1'R,2''S,4S,5R)-5-[(1-benzyl-5-oxo-pyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 583040-06-6
(1R,2S,3R,7R,8R,9S)-10-benzyl-2,8-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-4,6-dioxa-10-aza-tricyclo[7.2.1.0]dodecan-11-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 24h;
DOI:10.1021/jo0344539

Reference yield:

: 152611-51-3
(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

: 583040-06-6
(1R,2S,3R,7R,8R,9S)-10-benzyl-2,8-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-4,6-dioxa-10-aza-tricyclo[7.2.1.0]dodecan-11-one

Guidance literature:: Multi-step reaction with 7 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: 96 percent / NaIO₄ / CH₂Cl₂; H₂O / 1 h / 20 °C

7: 80 percent / diisopropylethylamine / CH₂Cl₂ / 24 h / 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; ammonium cerium(IV) nitrate; potassium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo0344539

Reference yield:

: 152611-53-5
N-tert-butoxycarbonyl-6,7;8,9-di-O-isopropylidene-2,3-dideoxy-D-glycero-D-galacto-nonono-1,4-lactam

: 583040-06-6
(1R,2S,3R,7R,8R,9S)-10-benzyl-2,8-bis-(tert-butyldimethylsilanyloxy)-5,5-dimethyl-4,6-dioxa-10-aza-tricyclo[7.2.1.0]dodecan-11-one

Guidance literature:: Multi-step reaction with 6 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: 96 percent / NaIO₄ / CH₂Cl₂; H₂O / 1 h / 20 °C

6: 80 percent / diisopropylethylamine / CH₂Cl₂ / 24 h / 25 °C

With 2,6-dimethylpyridine; sodium periodate; ammonium cerium(IV) nitrate; potassium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jo0344539