2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydropaclitaxel

Base Information

Chemical Name:2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydropaclitaxel
CAS No.:248272-48-2
Molecular Formula:C₄₅H₅₅NO₁₂Si
Molecular Weight:830.017
Hs Code.:

Synonyms:2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydropaclitaxel

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydropaclitaxel

Chemical Property:

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Technology Process of 2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydropaclitaxel

There total 1 articles about 2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydropaclitaxel 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:

: 530-62-1
1,1'-carbonyldiimidazole

: 2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-6,7-dehydropaclitaxel

: 2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydro-10-deacetyl-9,10-carbonato-paclitaxel

: 248272-48-2
2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydropaclitaxel

Guidance literature:: With 1H-imidazole; In dichloromethane; at 40 ℃; for 4h; Yield given; Yields of byproduct given;
DOI:10.1016/S0040-4020(99)00552-9

Reference yield: 86.0%

: 54322-10-0
glutaric acid monobenzyl ester

: 248272-48-2
2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydropaclitaxel

: 248272-50-6
2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-4-(O-benzylglutaryl)-6,7-dehydropaclitaxel

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In toluene; for 96h; Ambient temperature;
DOI:10.1016/S0040-4020(99)00552-9

Reference yield:

: 248272-48-2
2'-O-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-1,2-carbonato-6,7-dehydropaclitaxel

: 248272-54-0
2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-hydroxy-7-epipaclitaxel

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / DCC, DMAP / toluene / 96 h / Ambient temperature

2: 81 percent / OsO₄, N-methylmorpholine-N-oxide / H₂O; acetone / 40 h / Ambient temperature

3: 87 percent / H₂ / Pd/C / ethyl acetate / 2 h

4: 78 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

5: 94 percent / DCC, DMAP / toluene / 24 h / Ambient temperature

With dmap; osmium(VIII) oxide; hydrogen; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; hexane; water; ethyl acetate; acetone; toluene;
DOI:10.1016/S0040-4020(99)00552-9