Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester
• CAS No.: 188123-36-6
• Molecular Formula: C₁₅H₁₄INO₄
• Molecular Weight: 399.185

Synonyms:Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

Chemical Property of Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

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Technology Process of Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

There total 3 articles about Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl 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: 63.0%

Benzoic acid (1S,2R,3S,4R)-3-tert-butoxycarbonylamino-bicyclo[2.2.1]hept-5-en-2-yl ester (188123-35-5) → Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.03,8]dec-10-yl ester (188123-36-6)

Guidance literature:

With iodine; In dichloromethane; for 7h; Ambient temperature;

DOI:10.1016/S0040-4039(96)02402-1

Reference yield:

(+)-(1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.02,6]dec-8-en-4-one (139240-75-8) → Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.03,8]dec-10-yl ester (188123-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Et₃N, DMAP / tetrahydrofuran / 1 h / Ambient temperature

2: 95 percent / tetrahydrofuran / 0.17 h / -78 °C

3: 63 percent / I₂ / CH₂Cl₂ / 7 h / Ambient temperature

With dmap; iodine; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(96)02402-1

Reference yield:

(1S,2R,6S,7R)-4-Oxo-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-8-ene-5-carboxylic acid tert-butyl ester (188123-34-4) → Benzoic acid (1R,2R,3R,7S,8S,10R)-2-iodo-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.03,8]dec-10-yl ester (188123-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / tetrahydrofuran / 0.17 h / -78 °C

2: 63 percent / I₂ / CH₂Cl₂ / 7 h / Ambient temperature

With iodine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(96)02402-1

upstream raw materials:

Benzoic acid (1S,2R,3S,4R)-3-tert-butoxycarbonylamino-bicyclo[2.2.1]hept-5-en-2-yl ester

(+)-(1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.0^2,6]dec-8-en-4-one

(1S,2R,6S,7R)-4-Oxo-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-5-carboxylic acid tert-butyl ester

Downstream raw materials:

Benzoic acid (1S,3S,7S,8S,10R)-5-oxo-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]dec-10-yl ester

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-3-methyl-hexanoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-3-methyl-heptanoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

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