(2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol

Base Information

• Chemical Name: (2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol
• CAS No.: 131013-29-1
• Molecular Formula: C₂₂H₃₃NO₃
• Molecular Weight: 359.509

Synonyms:(2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol

Chemical Property of (2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol

There total 14 articles about (2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol 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:

(3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxole (2457-93-4) → (2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol (131013-29-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / CuI / tetrahydrofuran / a) 1 h at -50 deg C and 30 min at -30 deg C

2: 95 percent / pyridine / 24 h / 45 °C

3: 90 percent / NaN₃ / dimethylsulfoxide / 3 h / 80 °C

4: 84 percent / methanolic HCl / 12 h / Ambient temperature

5: 95 percent / pyridine / CH₂Cl₂ / 1 h at -50 deg C, 30 min at 0 deg C

6: 66 percent / H₂ / palladium black / ethyl acetate / 6 h / 760 Torr

7: 86 percent / pyridine / CH₂Cl₂ / from -78 deg C to r.t. over a period for 1 h

8: 100 percent / aq. formic acid / tetrahydrofuran / 2 h / Heating

9: 1) n-butyllithium, HMPA / 1) THF, hexan, 15 min at -78 deg C and 30 min at 0 deg C, 2) THF, 30 min at -78 deg C and 12 h at r.t.

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; formic acid; sodium azide; hydrogen; palladium; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jo00003a040

Reference yield:

6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose (131013-17-7) → (2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol (131013-29-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / pyridine / 24 h / 45 °C

2: 90 percent / NaN₃ / dimethylsulfoxide / 3 h / 80 °C

3: 84 percent / methanolic HCl / 12 h / Ambient temperature

4: 95 percent / pyridine / CH₂Cl₂ / 1 h at -50 deg C, 30 min at 0 deg C

5: 66 percent / H₂ / palladium black / ethyl acetate / 6 h / 760 Torr

6: 86 percent / pyridine / CH₂Cl₂ / from -78 deg C to r.t. over a period for 1 h

7: 100 percent / aq. formic acid / tetrahydrofuran / 2 h / Heating

8: 1) n-butyllithium, HMPA / 1) THF, hexan, 15 min at -78 deg C and 30 min at 0 deg C, 2) THF, 30 min at -78 deg C and 12 h at r.t.

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; formic acid; sodium azide; hydrogen; palladium; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jo00003a040

Reference yield:

phenylmagnesium chloride → (2S,3S,5S)-2-(phenylmethyl)-1-carbomethoxy-5-<(E)-nonen-1-yl>-3-pyrrolidinol (131013-29-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / CuI / tetrahydrofuran / a) 1 h at -50 deg C and 30 min at -30 deg C

2: 95 percent / pyridine / 24 h / 45 °C

3: 90 percent / NaN₃ / dimethylsulfoxide / 3 h / 80 °C

4: 84 percent / methanolic HCl / 12 h / Ambient temperature

5: 95 percent / pyridine / CH₂Cl₂ / 1 h at -50 deg C, 30 min at 0 deg C

6: 66 percent / H₂ / palladium black / ethyl acetate / 6 h / 760 Torr

7: 86 percent / pyridine / CH₂Cl₂ / from -78 deg C to r.t. over a period for 1 h

8: 100 percent / aq. formic acid / tetrahydrofuran / 2 h / Heating

9: 1) n-butyllithium, HMPA / 1) THF, hexan, 15 min at -78 deg C and 30 min at 0 deg C, 2) THF, 30 min at -78 deg C and 12 h at r.t.

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; formic acid; sodium azide; hydrogen; palladium; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1021/jo00003a040

upstream raw materials:

(2S,3S,5S)-5-formyl-2-(phenylmethyl)-1-carbomethoxy-3-pyrrolidinol

(3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxole

6-C-phenyl-3,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

6-C-phenyl-5-azido-3,5,6-trideoxy-1,2-O-isopropylidene-β-L-talofuranose

Downstream raw materials:

(+)-preussin

(2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol

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