(Z)-6-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-6-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl ester
• CAS No.: 250595-70-1
• Molecular Formula: C₃₆H₅₃NO₅Si
• Molecular Weight: 607.906
• Mol file: 250595-70-1.mol

Synonyms:(Z)-6-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl ester

Chemical Property of (Z)-6-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-6-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl ester

There total 10 articles about (Z)-6-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl 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:

methyl (2Z)-3-iodoprop-2-enoate (6214-23-9) + {1-allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-carbamic acid tert-butyl ester (250595-69-8) → (Z)-6-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl ester (250595-70-1)

Guidance literature:

{1-allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-carbamic acid tert-butyl ester; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran;

methyl (2Z)-3-iodoprop-2-enoate; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)01170-3

Reference yield:

(2-oxocyclopent)acetic acid (104115-44-8,1460-38-4) → (Z)-6-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl ester (250595-70-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95 percent / toluene / Heating

2.1: 99 percent / TiCl₄ / CH₂Cl₂ / -78 - 20 °C

3.1: 92 percent / Na; NH₃ / tetrahydrofuran; ethanol / -78 °C

4.1: 96 percent / DMAP / tetrahydrofuran

5.1: LiHMDS / tetrahydrofuran / -40 °C

5.2: 90 percent / tetrahydrofuran / -78 - 0 °C

6.1: 89 percent / LiOH; H₂O / tetrahydrofuran

7.1: NEt₃ / tetrahydrofuran

8.1: NaBH₄ / methanol

9.1: 95 percent / NEt₃; DMAP / CH₂Cl₂

10.1: 9-BBN / tetrahydrofuran

10.2: AsPh₃; Cs₂CO₃; H₂O / [Pd(dppf)Cl₂] / dimethylformamide

With dmap; lithium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; ammonia; water; sodium; titanium tetrachloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1.1: Cyclization / 2.1: Ring cleavage / 3.1: Reduction / 4.1: Acylation / 5.1: Metallation / 5.2: Methylation / 6.1: Hydrolysis / 7.1: Acylation / 8.1: Reduction / 9.1: Etherification / 10.1: Addition / 10.2: Alkylation;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I

Reference yield:

(3R,5aR,8aS)-3-phenyl-hexahydro-1-oxa-3a-aza-cyclopenta[c]pentalen-4-one (161779-70-0) → (Z)-6-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-hex-2-enoic acid methyl ester (250595-70-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 99 percent / TiCl₄ / CH₂Cl₂ / -78 - 20 °C

2.1: 92 percent / Na; NH₃ / tetrahydrofuran; ethanol / -78 °C

3.1: 96 percent / DMAP / tetrahydrofuran

4.1: LiHMDS / tetrahydrofuran / -40 °C

4.2: 90 percent / tetrahydrofuran / -78 - 0 °C

5.1: 89 percent / LiOH; H₂O / tetrahydrofuran

6.1: NEt₃ / tetrahydrofuran

7.1: NaBH₄ / methanol

8.1: 95 percent / NEt₃; DMAP / CH₂Cl₂

9.1: 9-BBN / tetrahydrofuran

9.2: AsPh₃; Cs₂CO₃; H₂O / [Pd(dppf)Cl₂] / dimethylformamide

With dmap; lithium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; ammonia; water; sodium; titanium tetrachloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1.1: Ring cleavage / 2.1: Reduction / 3.1: Acylation / 4.1: Metallation / 4.2: Methylation / 5.1: Hydrolysis / 6.1: Acylation / 7.1: Reduction / 8.1: Etherification / 9.1: Addition / 9.2: Alkylation;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I

upstream raw materials:

methyl (2Z)-3-iodoprop-2-enoate

{1-allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-carbamic acid tert-butyl ester

(2-oxocyclopent)acetic acid

(3R,5aR,8aS)-3-phenyl-hexahydro-1-oxa-3a-aza-cyclopenta[c]pentalen-4-one

Downstream raw materials:

{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-acetic acid methyl ester

C₃₇H₅₃NO₃Si

4-{(1R,5S,7R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-aza-spiro[4.5]dec-7-yl}-3-oxo-butyric acid tert-butyl ester

C₃₇H₅₃NO₄Si