(3S,4S,5R)-3-benzyloxy-1-(t-butoxycarbonyl)-5-<(1S)-1-hydroxy-1-(4-methoxyphenyl)methyl>-4-(2-tetrahydropyranyloxy)pyrrolidine

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Chemical Name:(3S,4S,5R)-3-benzyloxy-1-(t-butoxycarbonyl)-5-<(1S)-1-hydroxy-1-(4-methoxyphenyl)methyl>-4-(2-tetrahydropyranyloxy)pyrrolidine
CAS No.:160140-35-2
Molecular Formula:C₂₉H₃₉NO₇
Molecular Weight:513.631
Hs Code.:

Synonyms:(3S,4S,5R)-3-benzyloxy-1-(t-butoxycarbonyl)-5-<(1S)-1-hydroxy-1-(4-methoxyphenyl)methyl>-4-(2-tetrahydropyranyloxy)pyrrolidine

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Chemical Property of (3S,4S,5R)-3-benzyloxy-1-(t-butoxycarbonyl)-5-<(1S)-1-hydroxy-1-(4-methoxyphenyl)methyl>-4-(2-tetrahydropyranyloxy)pyrrolidine

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Technology Process of (3S,4S,5R)-3-benzyloxy-1-(t-butoxycarbonyl)-5-<(1S)-1-hydroxy-1-(4-methoxyphenyl)methyl>-4-(2-tetrahydropyranyloxy)pyrrolidine

There total 13 articles about (3S,4S,5R)-3-benzyloxy-1-(t-butoxycarbonyl)-5-<(1S)-1-hydroxy-1-(4-methoxyphenyl)methyl>-4-(2-tetrahydropyranyloxy)pyrrolidine 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: 80.0%

: 104-92-7
1-bromo-4-methoxy-benzene

: 160140-34-1
(3S,4S,5S)-3-benzyloxy-1-(t-butoxycarbonyl)-5-formyl-4-(2-tetrahydropyranyloxy)pyrrolidine

: 160140-35-2
(3S,4S,5R)-3-benzyloxy-1-(t-butoxycarbonyl)-5-<(1S)-1-hydroxy-1-(4-methoxyphenyl)methyl>-4-(2-tetrahydropyranyloxy)pyrrolidine

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)76839-0

Reference yield:

: 160140-29-4
(2S,3S)-1,2-epoxy-4-(4-methoxybenzyloxy)-3-(2-tetrahydropyranyloxy)butane

: 160140-35-2
(3S,4S,5R)-3-benzyloxy-1-(t-butoxycarbonyl)-5-<(1S)-1-hydroxy-1-(4-methoxyphenyl)methyl>-4-(2-tetrahydropyranyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 11 steps

1: NH₄Cl, NaN₃ / methanol; H₂O / 2 h / 75 °C

2: NaH / dimethylformamide / 1 h / 25 °C

3: 1.) triphenylphosphine, 2.) H₂O / 1.) THF, 50 deg C, 2 h, 2.) THF, 50 deg C, 2 h

4: NaHCO₃ / CH₂Cl₂; H₂O / 1 h / 25 °C

5: 95 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 25 °C

6: 1.) DMSO, oxalyl dichloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 to 0 deg C, 0.5 h

7: benzene / 0.25 h / 25 °C

8: NaHCO₃, MCPBA / CH₂Cl₂ / 48 h / 25 °C

9: BF₃*Et₂O / CH₂Cl₂ / 0.17 h / -78 °C

10: 1.) DMSO, oxalyl dichloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 to 0 deg C, 0.5 h

11: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 0.5 h

With n-butyllithium; sodium azide; oxalyl dichloride; boron trifluoride diethyl etherate; water; sodium hydride; sodium hydrogencarbonate; ammonium chloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1246/bcsj.67.3057

Reference yield:

: 160140-32-9
(3S,4S)-4-benzyloxy-5-(t-butoxycarbonylamino)-3-(2-tetrahydropyranyloxy)-1-pentene

: 160140-35-2
(3S,4S,5R)-3-benzyloxy-1-(t-butoxycarbonyl)-5-<(1S)-1-hydroxy-1-(4-methoxyphenyl)methyl>-4-(2-tetrahydropyranyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: NaHCO₃, MCPBA / CH₂Cl₂ / 48 h / 25 °C

2: BF₃*Et₂O / CH₂Cl₂ / 0.17 h / -78 °C

3: 1.) DMSO, oxalyl dichloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 to 0 deg C, 0.5 h

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 0.5 h

With n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1246/bcsj.67.3057