(1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid

Base Information

• Chemical Name: (1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid
• CAS No.: 850835-69-7
• Molecular Formula: C₂₈H₃₄O₆Si
• Molecular Weight: 494.66
• Mol file: 850835-69-7.mol

Synonyms:(1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid

Chemical Property of (1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid

There total 6 articles about (1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid 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: 93.0%

(1S,4aS,5S,7S,7aR)-4-formyl-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-1-yl acetate (850835-68-6) → (1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid (850835-69-7)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; for 48h;

DOI:10.1021/ja050064f

Reference yield:

(E)-(4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-oct-2-enedial → (1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid (850835-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: L-proline / dimethylsulfoxide / 5 h / 40 °C

1.2: 910 mg / pyridine; DMAP / dimethylsulfoxide / 0.25 h / 0 °C

2.1: POCl₃ / -20 - 20 °C

2.2: 73 percent / 60 h / 40 °C

3.1: 93 percent / NaClO₂; aq. NaH₂PO₄; 2-methylbut-2-ene / 2-methyl-propan-2-ol / 48 h

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; L-proline; trichlorophosphate; In dimethyl sulfoxide; tert-butyl alcohol; 1.1: intramolecular Michael addition;

DOI:10.1021/ja050064f

Reference yield:

(E,3R,5S)-7-(methoxycarbonyl)-5-hydroxy-3-methylhept-6-enyl 2,4,6-trimethylbenzoate (850835-63-1) → (1S,4aS,5S,7S,7aR)-1-acetoxy-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-4-carboxylic acid (850835-69-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / imidazole; DMAP / dimethylformamide / 12 h

2.1: 96 percent / diisobutylaluminum hydride / hexane; diethyl ether / 0.5 h / -78 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h

4.1: L-proline / dimethylsulfoxide / 5 h / 40 °C

4.2: 910 mg / pyridine; DMAP / dimethylsulfoxide / 0.25 h / 0 °C

5.1: POCl₃ / -20 - 20 °C

5.2: 73 percent / 60 h / 40 °C

6.1: 93 percent / NaClO₂; aq. NaH₂PO₄; 2-methylbut-2-ene / 2-methyl-propan-2-ol / 48 h

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diisobutylaluminium hydride; Dess-Martin periodane; L-proline; trichlorophosphate; In diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: intramolecular Michael addition;

DOI:10.1021/ja050064f

upstream raw materials:

(1S,4aS,5S,7S,7aR)-4-formyl-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-1-yl acetate

(E,3R,5S)-7-(methoxycarbonyl)-5-hydroxy-3-methylhept-6-enyl 2,4,6-trimethylbenzoate

(1S,4aR,5S,7S,7aR)-1,4a,5,6,7,7a-hexahydro-5-(tert-butyldiphenylsilanyloxy)-7-methylcyclopenta[c]pyran-1-yl acetate

(E,3R,5S)-7-(methoxycarbonyl)-5-(tert-butyldiphenylsilanyloxy)-3-methylhept-6-enyl 2,4,6-trimethylbenzoate

Downstream raw materials:

(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester