(2S,3R)-benzyl-3-tert-butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Base Information

• Chemical Name: (2S,3R)-benzyl-3-tert-butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• CAS No.: 222855-48-3
• Molecular Formula: C₂₃H₂₇NO₄
• Molecular Weight: 381.472
• Mol file: 222855-48-3.mol

Synonyms:

Chemical Property of (2S,3R)-benzyl-3-tert-butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-benzyl-3-tert-butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylate

There total 9 articles about (2S,3R)-benzyl-3-tert-butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylate 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:

ethyl 1,4-dihydronapthalene-2-carboxylate (82584-13-2) → (2S,3R)-benzyl-3-tert-butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylate (222855-48-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 71 percent / DIBAL-H / tetrahydrofuran / -70 °C

2: 61 percent / t-BuOOH, Ti(OiPr)4, (+)-diethyltartarate

3: Dess Martin periodinane

4: NaClO₂, Na₂HPO₄ / 2-methyl-propan-2-ol; H₂O

5: EDC, DMAP

6: NaN₃, NH₄Cl / ethanol

7: Ph₃P / acetonitrile

8: 1.) SmI₂

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; disodium hydrogenphosphate; sodium azide; samarium diiodide; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; (+)-Weinsaeure-diethylester; triphenylphosphine; In tetrahydrofuran; ethanol; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00205-1

Reference yield:

α,α'-dibromo-o-xylene (91-13-4) → (2S,3R)-benzyl-3-tert-butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylate (222855-48-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 43 percent / CrCl₂, AlCl₃ / tetrahydrofuran

2: 71 percent / DIBAL-H / tetrahydrofuran / -70 °C

3: 61 percent / t-BuOOH, Ti(OiPr)4, (+)-diethyltartarate

4: Dess Martin periodinane

5: NaClO₂, Na₂HPO₄ / 2-methyl-propan-2-ol; H₂O

6: EDC, DMAP

7: NaN₃, NH₄Cl / ethanol

8: Ph₃P / acetonitrile

9: 1.) SmI₂

With chromium dichloride; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; disodium hydrogenphosphate; aluminium trichloride; sodium azide; samarium diiodide; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; (+)-Weinsaeure-diethylester; triphenylphosphine; In tetrahydrofuran; ethanol; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00205-1

Reference yield:

2,7-dihydro-1aH-1-oxa-cyclopropa[b]naphthalene-7a-carbaldehyde → (2S,3R)-benzyl-3-tert-butoxycarbonylamino-1,2,3,4-tetrahydronaphthalene-2-carboxylate (222855-48-3)

Guidance literature:

Multi-step reaction with 5 steps

1: NaClO₂, Na₂HPO₄ / 2-methyl-propan-2-ol; H₂O

2: EDC, DMAP

3: NaN₃, NH₄Cl / ethanol

4: Ph₃P / acetonitrile

5: 1.) SmI₂

With dmap; sodium chlorite; disodium hydrogenphosphate; sodium azide; samarium diiodide; ammonium chloride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; In ethanol; water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00205-1

upstream raw materials:

di-tert-butyl dicarbonate

(1aR,7aS)-1,1a,2,7-Tetrahydro-1-aza-cyclopropa[b]naphthalene-7a-carboxylic acid benzyl ester

ethyl 1,4-dihydronapthalene-2-carboxylate

α,α'-dibromo-o-xylene