di-tert-butyl (8S)-8β-carboxylic acid-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.0^2,6.0^3,5]decane-3,5-dicarboxylate

Base Information

• Chemical Name: di-tert-butyl (8S)-8β-carboxylic acid-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.0^2,6.0^3,5]decane-3,5-dicarboxylate
• CAS No.: 634893-97-3
• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.438
• Mol file: 634893-97-3.mol

Synonyms:di-tert-butyl (8S)-8β-carboxylic acid-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.0^2,6.0^3,5]decane-3,5-dicarboxylate

Chemical Property of di-tert-butyl (8S)-8β-carboxylic acid-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.0^2,6.0^3,5]decane-3,5-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of di-tert-butyl (8S)-8β-carboxylic acid-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.0^2,6.0^3,5]decane-3,5-dicarboxylate

There total 1 articles about di-tert-butyl (8S)-8β-carboxylic acid-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.0^2,6.0^3,5]decane-3,5-dicarboxylate 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:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) → di-tert-butyl (8S)-8β-carboxylic acid-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.02,6.03,5]decane-3,5-dicarboxylate (634893-97-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / Et₃N; EDCI; DMAP / CH₂Cl₂ / 12 h / 20 °C

2: 70 percent / RuH₂(CO)(PPh₃) / benzene / 24 h / 80 °C

3: 87 percent / TBHP; t-BuOK / tetrahydrofuran; toluene / 12 h / 20 °C

4: H₂; aq. AcOH / 10percent Pd/C / ethyl acetate / 24 h

With tert.-butylhydroperoxide; dmap; potassium tert-butylate; hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; (Ph₃P)Ru(CO)H₂; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; benzene; 2: Mitsudo reaction;

DOI:10.1039/b301980b

Reference yield: 58.0%

Gly-OBz (1738-68-7) + di-tert-butyl (8S)-8β-carboxylic acid-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.02,6.03,5]decane-3,5-dicarboxylate (634893-97-3) → di-tert-butyl (8S)-8β-(benzyloxycarbonylmethylcarbamoyl)-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.02,6.03,5]decane-3,5-dicarboxylate (634893-98-4)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1039/b301980b

Reference yield:

di-tert-butyl (8S)-8β-carboxylic acid-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.02,6.03,5]decane-3,5-dicarboxylate (634893-97-3) → di-tert-butyl (4S,11S)-4β-(benzyloxycarbonylmethylcarbamoyl)-11β-(1-methoxycarbonylethylcarbamoyl)-16-oxa-(1α,2β,3α,6α,7β,8α,9β,10α,13α,14β)-hexacyclo[6.6.1.14,6.110,13.02,7.09,14]heptadeca-1,8-dicarboxylate (634893-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / diisopropylethylamine; EDCI; HOBt / dimethylformamide / 12 h / 20 °C

2: 70 percent / CH₂Cl₂ / 12 h / 130 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b301980b

upstream raw materials:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Downstream raw materials:

di-tert-butyl (8S)-8β-(benzyloxycarbonylmethylcarbamoyl)-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.0^2,6.0^3,5]decane-3,5-dicarboxylate

di-tert-butyl (4S,11S)-4β-(benzyloxycarbonylmethylcarbamoyl)-11β-(1-methoxycarbonylethylcarbamoyl)-16-oxa-(1α,2β,3α,6α,7β,8α,9β,10α,13α,14β)-hexacyclo[6.6.1.1^4,6.1^10,13.0^2,7.0^9,14]heptadeca-1,8-dicarboxylate