N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester

Base Information

• Chemical Name: N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester
• CAS No.: 327037-84-3
• Molecular Formula: C₃₉H₅₁N₂O₈P
• Molecular Weight: 706.816

Synonyms:N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester

Chemical Property of N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester

There total 40 articles about N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl 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: 37.0%

phosphoric acid dibenzyl ester (1623-08-1) + [(1S,3S,6S,7S,8S,9R)-7,9-Dihydroxy-6-(4-methoxy-benzyl)-5-aza-tricyclo[6.3.1.01,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester (327037-83-2) → N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.01.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester (327037-84-3)

Guidance literature:

With di-isopropyl azodicarboxylate; triethylamine; tri(4-chlorophenyl)phosphine; In toluene; at 20 ℃; for 26h;

DOI:10.1002/1521-3773(20001215)39:24<4593::AID-ANIE4593>3.0.CO;2-X

Reference yield:

methyl (S)-2-amino-3-(4-methoxyphenyl)propionate (17355-19-0) → N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.01.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester (327037-84-3)

Guidance literature:

Multi-step reaction with 10 steps

1: NaBH(OAc)3; molecular sieves 4 Angstroem / 25 h / 0 - 20 °C

2: 51 percent / PhI(OAc)2 / various solvent(s) / 0.17 h / 20 °C

3: NaSPh / dimethylsulfoxide / 3 h / 20 °C

4: pyridine / 12 h / 20 °C

5: 93 percent / H₂ / Raney Ni / ethanol; ethyl acetate / 15 h / 20 °C

6: 90 percent / LiAlH₄ / tetrahydrofuran / 3 h / -78 - 0 °C

7: 100 percent / (COCl)2; DMSO; DIEA / CH₂Cl₂ / 0.5 h / -78 °C

8: 34 percent / NaOMe / methanol / 2 h / 0 °C

9: 92 percent / H₂ / Raney Ni / ethanol; ethyl acetate / 4 h / 20 °C

10: 37 percent / tris(4-chlorophenyl)phosphine; DIAD; NEt₃ / toluene / 26 h / 20 °C

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; 4 A molecular sieve; hydrogen; sodium methylate; sodium thiophenolate; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tri(4-chlorophenyl)phosphine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; 7: Swern oxidation / 10: Mitsunobu reaction;

DOI:10.1002/1521-3773(20001215)39:24<4593::AID-ANIE4593>3.0.CO;2-X

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.01.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester (327037-84-3)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 12 h / 20 °C

2: 93 percent / H₂ / Raney Ni / ethanol; ethyl acetate / 15 h / 20 °C

3: 90 percent / LiAlH₄ / tetrahydrofuran / 3 h / -78 - 0 °C

4: 100 percent / (COCl)2; DMSO; DIEA / CH₂Cl₂ / 0.5 h / -78 °C

5: 34 percent / NaOMe / methanol / 2 h / 0 °C

6: 92 percent / H₂ / Raney Ni / ethanol; ethyl acetate / 4 h / 20 °C

7: 37 percent / tris(4-chlorophenyl)phosphine; DIAD; NEt₃ / toluene / 26 h / 20 °C

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; di-isopropyl azodicarboxylate; hydrogen; sodium methylate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tri(4-chlorophenyl)phosphine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; toluene; 4: Swern oxidation / 7: Mitsunobu reaction;

DOI:10.1002/1521-3773(20001215)39:24<4593::AID-ANIE4593>3.0.CO;2-X

upstream raw materials:

phosphoric acid dibenzyl ester

[(1S,3S,6S,7S,8S,9R)-7,9-Dihydroxy-6-(4-methoxy-benzyl)-5-aza-tricyclo[6.3.1.0^1,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester

cyclohexanedione monoethylene ketal

di-tert-butyl dicarbonate

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