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

Base Information

• Chemical Name: 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
• CAS No.: 634893-98-4
• Molecular Formula: C₂₉H₃₇NO₈
• Molecular Weight: 527.615

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 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

There total 4 articles about 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 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: 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:

(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-(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:

Multi-step reaction with 5 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

5: 58 percent / diisopropylethylamine; EDCI; HOBt / dimethylformamide / 12 h / 20 °C

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

DOI:10.1039/b301980b

Reference yield:

Di-tert-butyl acetylenedicarboxylate (66086-33-7) → 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:

Multi-step reaction with 4 steps

1: 70 percent / RuH₂(CO)(PPh₃) / benzene / 24 h / 80 °C

2: 87 percent / TBHP; t-BuOK / tetrahydrofuran; toluene / 12 h / 20 °C

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

4: 58 percent / diisopropylethylamine; EDCI; HOBt / dimethylformamide / 12 h / 20 °C

With tert.-butylhydroperoxide; potassium tert-butylate; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; (Ph₃P)Ru(CO)H₂; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 1: Mitsudo reaction;

DOI:10.1039/b301980b

upstream raw materials:

Gly-OBz

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

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

Di-tert-butyl acetylenedicarboxylate

Downstream raw materials:

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

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