7-benzyloxy-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-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-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester
CAS No.:503867-79-6
Molecular Formula:C₂₅H₂₉NO₈
Molecular Weight:471.507
Hs Code.:

7-benzyloxy-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-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-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-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-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-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-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

There total 17 articles about 7-benzyloxy-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-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: 50.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 503311-49-7
7-benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

: 503867-79-6
7-benzyloxy-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

: 7-benzyloxy-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 0 ℃; for 5h;
DOI:10.1021/jo049862z

Reference yield:

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

: 503867-79-6
7-benzyloxy-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-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 5 steps

1: 324 mg / H₂ / Pt/C / methanol / 2 h / 20 °C / 760 Torr

2: TsOH*H₂O / CH₂Cl₂ / 0.17 h / 20 °C

3: 164 mg / TBAF / tetrahydrofuran / 12 h / 20 °C

4: 82 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 50 percent / aq. LiOH / tetrahydrofuran / 5 h / 0 °C

With lithium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 4: Swern oxidation;
DOI:10.1021/jo049862z

Reference yield:

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

: 503867-79-6
7-benzyloxy-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-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: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 - 20 °C

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

3: TsOH*H₂O / CH₂Cl₂ / 0.17 h / 20 °C

4: 164 mg / TBAF / tetrahydrofuran / 12 h / 20 °C

5: 82 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6: 50 percent / aq. LiOH / tetrahydrofuran / 5 h / 0 °C

With lithium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 5: Swern oxidation;
DOI:10.1021/jo049862z