di-tert-butyl (8S)-8β-benzyloxycarbonyl-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-benzyloxycarbonyl-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.0^2,6.0^3,5]decane-3,5-dicarboxylate
• CAS No.: 634893-88-2
• Molecular Formula: C₂₇H₃₄O₇
• Molecular Weight: 470.563

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

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

There total 3 articles about di-tert-butyl (8S)-8β-benzyloxycarbonyl-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: 87.0%

di-tert-butyl (7S)-7β-benzyloxycarbonyl-(1α,2β,5β,6α)-tricyclo[4.2.1.02,5]nona-3-ene-3,4-dicarboxylate (634893-89-3) → di-tert-butyl (8S)-8β-benzyloxycarbonyl-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.02,6.03,5]decane-3,5-dicarboxylate (634893-88-2)

Guidance literature:

With tert.-butylhydroperoxide; potassium tert-butylate; In tetrahydrofuran; toluene; 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-benzyloxycarbonyl-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.02,6.03,5]decane-3,5-dicarboxylate (634893-88-2)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1039/b301980b

Reference yield:

Di-tert-butyl acetylenedicarboxylate (66086-33-7) → di-tert-butyl (8S)-8β-benzyloxycarbonyl-4-oxa-(1α,2β,3α,5α,6β,7α)-tetracyclo[5.2.1.02,6.03,5]decane-3,5-dicarboxylate (634893-88-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With tert.-butylhydroperoxide; potassium tert-butylate; (Ph₃P)Ru(CO)H₂; In tetrahydrofuran; toluene; benzene; 1: Mitsudo reaction;

DOI:10.1039/b301980b

upstream raw materials:

di-tert-butyl (7S)-7β-benzyloxycarbonyl-(1α,2β,5β,6α)-tricyclo[4.2.1.0^2,5]nona-3-ene-3,4-dicarboxylate

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

Di-tert-butyl acetylenedicarboxylate

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