7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

Base Information

Chemical Name:7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester
CAS No.:503311-47-5
Molecular Formula:C₂₉H₄₁NO₆Si
Molecular Weight:527.733
Hs Code.:

7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[<i>a</i>]cyclopropa[<i>e</i>]cyclooctene-5-carboxylic acid methyl ester

Synonyms:7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

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Chemical Property of 7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

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Technology Process of 7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

There total 14 articles about 7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester 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:

: 503867-76-3
methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-formyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

: 503311-47-5
7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 2h;
DOI:10.1002/anie.200290016

Reference yield:

: 503311-45-3
methyl 3-benzyloxy-4-[(2S)-2-[(2R,3R)-3-hydroxymethyloxiran-2-yl]-2-triisopropylsilyloxyethyl]-5-nitrobenzoate

: 503311-47-5
7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 - 20 °C

2: 324 mg / H₂ / Pt/C / methanol / 2 h / 20 °C / 760 Torr

With hydrogen; Dess-Martin periodane; platinum on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/jo049862z

Reference yield:

: 503311-42-0
methyl 3-benzyloxy-5-nitro-4-[(2S,3R,4S)-3,4,5-trihydroxy-2-triisopropylsilyloxypentyl]benzoate

: 503311-47-5
7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N; DMAP / CH₂Cl₂ / 13 h / 20 °C

2: DABCO / CH₂Cl₂ / 1.5 h / 20 °C

3: 2.82 g / NaH / dimethylformamide / 1 h / 20 °C

4: CSA / methanol / 1 h / 20 °C

5: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 - 20 °C

6: 324 mg / H₂ / Pt/C / methanol / 2 h / 20 °C / 760 Torr

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; camphor-10-sulfonic acid; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine; platinum on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo049862z