(S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:182053-14-1
Molecular Formula:C₂₉H₄₁NO₅
Molecular Weight:483.648
Hs Code.:

Synonyms:(S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl ester

There total 13 articles about (S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl 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:

: 63527-49-1
(R)-2-methylpent-4-enoic acid

: 182053-14-1
(S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: LiAlH₄ / diethyl ether / 4 h / Ambient temperature

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, RT, 1.5 h

3: 1.) Ph₃P / 1.) CH₂Cl₂, -14 deg C, 2.) CH₂Cl₂, 0 deg C, 1.5 h

4: OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol

5: 1.) NaIO₄, 2.) H₂O / 1.) THF, 2.) THF, 1 h

6: 97 percent / CH₂Cl₂ / 48 h / Heating

7: 98 percent / iBu₃Al / pentane; toluene / 1 h / Ambient temperature

8: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

9: 84 percent / TsOH / acetone / 30 h / Ambient temperature

10: 94 percent / nBuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

11: 1.) nBuLi, 2.) Et₂AlCl

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; water; triisobutylaluminum; diethylaluminium chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; pentane;
DOI:10.1021/ja961641q

Reference yield:

: 63501-27-9
(2R)-2-methyl-4-penten-1-ol

: 182053-14-1
(S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, RT, 1.5 h

2: 1.) Ph₃P / 1.) CH₂Cl₂, -14 deg C, 2.) CH₂Cl₂, 0 deg C, 1.5 h

3: OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol

4: 1.) NaIO₄, 2.) H₂O / 1.) THF, 2.) THF, 1 h

5: 97 percent / CH₂Cl₂ / 48 h / Heating

6: 98 percent / iBu₃Al / pentane; toluene / 1 h / Ambient temperature

7: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

8: 84 percent / TsOH / acetone / 30 h / Ambient temperature

9: 94 percent / nBuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

10: 1.) nBuLi, 2.) Et₂AlCl

With sodium periodate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; water; triisobutylaluminum; diethylaluminium chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; pentane;
DOI:10.1021/ja961641q

Reference yield:

: 137895-73-9
(R)-5,5-dibromo-3-methyl-4-pentenal

: 182053-14-1
(S)-2-[(E)-(1S,5R)-1-Hydroxy-1,5-dimethyl-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-non-7-en-3-ynyl]-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / CH₂Cl₂ / 48 h / Heating

2: 98 percent / iBu₃Al / pentane; toluene / 1 h / Ambient temperature

3: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

4: 84 percent / TsOH / acetone / 30 h / Ambient temperature

5: 94 percent / nBuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

6: 1.) nBuLi, 2.) Et₂AlCl

With n-butyllithium; tetrabutyl ammonium fluoride; triisobutylaluminum; diethylaluminium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene; pentane;
DOI:10.1021/ja961641q