33-(tert-butyldimethylsilyl)-22-dihydro-22-(methoxycarbonyl)methyl-ascomycin

Base Information

• Chemical Name: 33-(tert-butyldimethylsilyl)-22-dihydro-22-(methoxycarbonyl)methyl-ascomycin
• CAS No.: 307953-22-6
• Molecular Formula: C₅₂H₈₉NO₁₄Si
• Molecular Weight: 980.362
• Mol file: 307953-22-6.mol

Synonyms:33-(tert-butyldimethylsilyl)-22-dihydro-22-(methoxycarbonyl)methyl-ascomycin

Chemical Property of 33-(tert-butyldimethylsilyl)-22-dihydro-22-(methoxycarbonyl)methyl-ascomycin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 33-(tert-butyldimethylsilyl)-22-dihydro-22-(methoxycarbonyl)methyl-ascomycin

There total 1 articles about 33-(tert-butyldimethylsilyl)-22-dihydro-22-(methoxycarbonyl)methyl-ascomycin 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: 36.0%

ketene t-butyldimethylsilyl methyl acetal (77086-38-5) + 33-O-(tert-butyldimethylsilyl)-ascomycin (133941-74-9) → 33-(tert-butyldimethylsilyl)-22-dihydro-22-(methoxycarbonyl)methyl-ascomycin (307953-22-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - -30 ℃; for 3h;

DOI:10.1016/S0040-4020(00)00669-4

Reference yield: 64.0%

33-(tert-butyldimethylsilyl)-22-dihydro-22-(methoxycarbonyl)methyl-ascomycin (307953-22-6) → 22-dihydro-24-deoxy-(22b-oxo-tetrahydropyrano[22,24-b,c])-ascomycin

Guidance literature:

With hydrogenchloride; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00669-4

Reference yield:

33-(tert-butyldimethylsilyl)-22-dihydro-22-(methoxycarbonyl)methyl-ascomycin (307953-22-6) → 22-deoxo-24-deoxy-(22b-oxo-22,22a-dihydropyrano[22,24-b,c])-ascomycin

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / 1N HCl / acetonitrile / 1 h / 20 °C

2: 12 percent / p-TsOH / toluene / 16 h / 60 °C

With hydrogenchloride; toluene-4-sulfonic acid; In toluene; acetonitrile; 1: Cyclization / 2: Dehydration;

DOI:10.1016/S0040-4020(00)00669-4

upstream raw materials:

ketene t-butyldimethylsilyl methyl acetal

33-O-(tert-butyldimethylsilyl)-ascomycin