Benzyl-{(R)-1-benzyloxymethyl-2-[(R)-2-hydroxymethyl-cyclopent-(Z)-ylidene]-ethyl}-carbamic acid tert-butyl ester

Base Information

Chemical Name:Benzyl-{(R)-1-benzyloxymethyl-2-[(R)-2-hydroxymethyl-cyclopent-(Z)-ylidene]-ethyl}-carbamic acid tert-butyl ester
CAS No.:345341-69-7
Molecular Formula:C₂₈H₃₇NO₄
Molecular Weight:451.606
Hs Code.:

Synonyms:Benzyl-{(R)-1-benzyloxymethyl-2-[(R)-2-hydroxymethyl-cyclopent-(Z)-ylidene]-ethyl}-carbamic acid tert-butyl ester

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Chemical Property of Benzyl-{(R)-1-benzyloxymethyl-2-[(R)-2-hydroxymethyl-cyclopent-(Z)-ylidene]-ethyl}-carbamic acid tert-butyl ester

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Technology Process of Benzyl-{(R)-1-benzyloxymethyl-2-[(R)-2-hydroxymethyl-cyclopent-(Z)-ylidene]-ethyl}-carbamic acid tert-butyl ester

There total 16 articles about Benzyl-{(R)-1-benzyloxymethyl-2-[(R)-2-hydroxymethyl-cyclopent-(Z)-ylidene]-ethyl}-carbamic 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: 95.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 515835-51-5
{(R)-2-[(R)-2-Benzylamino-3-benzyloxy-prop-(Z)-ylidene]-cyclopentyl}-methanol

: 345341-69-7
Benzyl-{(R)-1-benzyloxymethyl-2-[(R)-2-hydroxymethyl-cyclopent-(Z)-ylidene]-ethyl}-carbamic acid tert-butyl ester

Guidance literature:: In dichloromethane; for 17h;
DOI:10.1021/jo026663b

Reference yield:

: 17497-52-8
1-iodocyclopentene

: 345341-69-7
Benzyl-{(R)-1-benzyloxymethyl-2-[(R)-2-hydroxymethyl-cyclopent-(Z)-ylidene]-ethyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: S-BuLi / tetrahydrofuran; cyclohexane / 3 h / -40 °C

1.2: 86 percent / tetrahydrofuran; cyclohexane / 3 h / -78 °C

2.1: CeCl₃; NaBH₄ / tetrahydrofuran; methanol / 2 h / 0 °C

3.1: TFA / CH₂Cl₂ / 0.5 h

4.1: DIEA

5.1: 18-crown-6; KH / tetrahydrofuran / 0.5 h / 20 °C

5.2: 3.0 g / n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

6.1: 96 percent HCOOH / Pd(OH)2/C / methanol / 0.33 h

7.1: 95 percent / CH₂Cl₂ / 17 h

With sodium tetrahydroborate; formic acid; cerium(III) chloride; 18-crown-6 ether; sec.-butyllithium; potassium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; 2.1: Luche reduction / 5.2: Still-Wittig rearrangement;
DOI:10.1021/jo026663b

Reference yield:

: 10080-41-8
cyclopentanone hydrazone

: 345341-69-7
Benzyl-{(R)-1-benzyloxymethyl-2-[(R)-2-hydroxymethyl-cyclopent-(Z)-ylidene]-ethyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: I₂; tetramethylguanidine / diethyl ether

2.1: S-BuLi / tetrahydrofuran; cyclohexane / 3 h / -40 °C

2.2: 86 percent / tetrahydrofuran; cyclohexane / 3 h / -78 °C

3.1: CeCl₃; NaBH₄ / tetrahydrofuran; methanol / 2 h / 0 °C

4.1: TFA / CH₂Cl₂ / 0.5 h

5.1: DIEA

6.1: 18-crown-6; KH / tetrahydrofuran / 0.5 h / 20 °C

6.2: 3.0 g / n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

7.1: 96 percent HCOOH / Pd(OH)2/C / methanol / 0.33 h

8.1: 95 percent / CH₂Cl₂ / 17 h

With sodium tetrahydroborate; formic acid; cerium(III) chloride; 18-crown-6 ether; 1,1,3,3-tetramethylguanidine; iodine; sec.-butyllithium; potassium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; 3.1: Luche reduction / 6.2: Still-Wittig rearrangement;
DOI:10.1021/jo026663b