(3aS,5R,6S,6aS)-{5-(tert-butyldimethylsilanyloxy)-6-[(3S,4S)-3-tert-butyldimethylsilanyloxy-4-methylnona-1,6-diynyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}acetic acid [(2R,1S)-2-(1-methyl-1-phenylethyl)-1-cyclohexyl ester]

Base Information

• Chemical Name: (3aS,5R,6S,6aS)-{5-(tert-butyldimethylsilanyloxy)-6-[(3S,4S)-3-tert-butyldimethylsilanyloxy-4-methylnona-1,6-diynyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}acetic acid [(2R,1S)-2-(1-methyl-1-phenylethyl)-1-cyclohexyl ester]
• CAS No.: 597557-62-5
• Molecular Formula: C₄₇H₇₄O₄Si₂
• Molecular Weight: 759.273

Synonyms:(3aS,5R,6S,6aS)-{5-(tert-butyldimethylsilanyloxy)-6-[(3S,4S)-3-tert-butyldimethylsilanyloxy-4-methylnona-1,6-diynyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}acetic acid [(2R,1S)-2-(1-methyl-1-phenylethyl)-1-cyclohexyl ester]

Chemical Property of (3aS,5R,6S,6aS)-{5-(tert-butyldimethylsilanyloxy)-6-[(3S,4S)-3-tert-butyldimethylsilanyloxy-4-methylnona-1,6-diynyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}acetic acid [(2R,1S)-2-(1-methyl-1-phenylethyl)-1-cyclohexyl ester]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,5R,6S,6aS)-{5-(tert-butyldimethylsilanyloxy)-6-[(3S,4S)-3-tert-butyldimethylsilanyloxy-4-methylnona-1,6-diynyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}acetic acid [(2R,1S)-2-(1-methyl-1-phenylethyl)-1-cyclohexyl ester]

There total 23 articles about (3aS,5R,6S,6aS)-{5-(tert-butyldimethylsilanyloxy)-6-[(3S,4S)-3-tert-butyldimethylsilanyloxy-4-methylnona-1,6-diynyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}acetic acid [(2R,1S)-2-(1-methyl-1-phenylethyl)-1-cyclohexyl 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: 98.0%

(-)-(E,3aS,4S,5R,6aS)-{5-(tert-butyldimethylsilanyloxy)-4-[(3S)-tert-butyldimethylsilanyloxy-4S-methylnona-1,6-diynyl]-hexahydropentalen-2-ylidene}acetic acid 2R-(1-methyl-1-phenylethyl)-1S-cyclohexyl ester (597557-38-5) → (3aS,5R,6S,6aS)-{5-(tert-butyldimethylsilanyloxy)-6-[(3S,4S)-3-tert-butyldimethylsilanyloxy-4-methylnona-1,6-diynyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}acetic acid [(2R,1S)-2-(1-methyl-1-phenylethyl)-1-cyclohexyl ester] (597557-62-5)

Guidance literature:

With lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide; In tetrahydrofuran; hexane; at -105 - -78 ℃; for 1.75h;

DOI:10.1021/ja030200l

Reference yield:

(3a'R,6a'S)-5,5-dimethyltetrahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'(3'H)-one (112755-94-9,92007-37-9) → (3aS,5R,6S,6aS)-{5-(tert-butyldimethylsilanyloxy)-6-[(3S,4S)-3-tert-butyldimethylsilanyloxy-4-methylnona-1,6-diynyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}acetic acid [(2R,1S)-2-(1-methyl-1-phenylethyl)-1-cyclohexyl ester] (597557-62-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium (R,R)-bis(phenylethyl)amide / tetrahydrofuran; hexane / 1 h / -105 °C

1.2: tetrahydrofuran; hexane / 1.67 h / -105 - -78 °C

1.3: NaBH₄ / tetrahydrofuran; hexane; ethanol / 4 h / -78 - -40 °C

2.1: LDA / tetrahydrofuran / 1 h / -78 °C

3.1: imidazole / dimethylformamide / 16 h / 20 °C

4.1: DIBALH / toluene; hexane / 3 h / -78 °C

5.1: t-BuOK / tetrahydrofuran / 0.33 h

5.2: t-BuOK / tetrahydrofuran / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 - 20 °C

6.2: tetrahydrofuran; hexane / 0.67 h / -19 °C

7.1: catecholborane; chiral oxazaborolidine / CH₂Cl₂; benzene-d6 / 4.5 h / -78 °C

8.1: aq. TsOH / acetone / 72 h / 20 °C

9.1: 1.76 g / imidazole / dimethylformamide / 14 h / 20 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 - 20 °C

10.2: 90 percent / tetrahydrofuran; hexane / -62 - -30 °C

11.1: 98 percent / lithium (R,R)-bis(phenylethyl)amide / tetrahydrofuran; hexane / 1.75 h / -105 - -78 °C

With 1H-imidazole; n-butyllithium; chiral oxazaborolidine; potassium tert-butylate; diisobutylaluminium hydride; lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide; toluene-4-sulfonic acid; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; In tetrahydrofuran; hexane; dichloromethane; benzene-d6; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja030200l

Reference yield:

1-iodo-2-pentyne (34498-11-8) → (3aS,5R,6S,6aS)-{5-(tert-butyldimethylsilanyloxy)-6-[(3S,4S)-3-tert-butyldimethylsilanyloxy-4-methylnona-1,6-diynyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}acetic acid [(2R,1S)-2-(1-methyl-1-phenylethyl)-1-cyclohexyl ester] (597557-62-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaN(SiMe₃)2 / tetrahydrofuran / 1 h / -78 °C

1.2: 93 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 81 percent / Ti(OEt)4 / 8 h / Heating

3.1: 92 percent / i-PrMgCl / tetrahydrofuran / 0.5 h / -19 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 - 20 °C

4.2: tetrahydrofuran; hexane / 0.67 h / -19 °C

5.1: catecholborane; chiral oxazaborolidine / CH₂Cl₂; benzene-d6 / 4.5 h / -78 °C

6.1: aq. TsOH / acetone / 72 h / 20 °C

7.1: 1.76 g / imidazole / dimethylformamide / 14 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 - 20 °C

8.2: 90 percent / tetrahydrofuran; hexane / -62 - -30 °C

9.1: 98 percent / lithium (R,R)-bis(phenylethyl)amide / tetrahydrofuran; hexane / 1.75 h / -105 - -78 °C

With 1H-imidazole; titanium(IV) tetraethanolate; n-butyllithium; chiral oxazaborolidine; isopropylmagnesium chloride; sodium hexamethyldisilazane; lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide; toluene-4-sulfonic acid; benzo[1,3,2]dioxaborole; In tetrahydrofuran; hexane; dichloromethane; benzene-d6; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja030200l

upstream raw materials:

(-)-(E,3aS,4S,5R,6aS)-{5-(tert-butyldimethylsilanyloxy)-4-[(3S)-tert-butyldimethylsilanyloxy-4S-methylnona-1,6-diynyl]-hexahydropentalen-2-ylidene}acetic acid 2R-(1-methyl-1-phenylethyl)-1S-cyclohexyl ester

1-iodo-2-pentyne

(3a'R,6a'S)-5,5-dimethyltetrahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'(3'H)-one

(+)-(3aS,4S,5R,6aS)-5-hydroxy-4-((3S)-hydroxy-4(S)-methylnona-1,6-diynyl)hexahydropentalen-2-one

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