2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-(2-benzyloxyacetoxy)-7-epipaclitaxel

Base Information

Chemical Name:2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-(2-benzyloxyacetoxy)-7-epipaclitaxel
CAS No.:248272-55-1
Molecular Formula:C₇₂H₈₃NO₁₉Si
Molecular Weight:1294.53
Hs Code.:

Synonyms:2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-(2-benzyloxyacetoxy)-7-epipaclitaxel

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Chemical Property of 2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-(2-benzyloxyacetoxy)-7-epipaclitaxel

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Technology Process of 2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-(2-benzyloxyacetoxy)-7-epipaclitaxel

There total 7 articles about 2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-(2-benzyloxyacetoxy)-7-epipaclitaxel 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: 85.0%

: 19810-31-2
Benzyloxyacetyl chloride

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

: 248272-55-1
2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-(2-benzyloxyacetoxy)-7-epipaclitaxel

Guidance literature:: With dmap; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(99)00552-9

Reference yield:

: 54322-10-0
glutaric acid monobenzyl ester

: 248272-55-1
2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-(2-benzyloxyacetoxy)-7-epipaclitaxel

Guidance literature:: Multi-step reaction with 6 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

6: 85 percent / DMAP / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; osmium(VIII) oxide; hydrogen; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; acetone; toluene;
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

: 248272-55-1
2'-O-(tert-butyldimethylsilyl)-4-deacetyl-4-(O-benzylglutaryl)-6α-(2-benzyloxyacetoxy)-7-epipaclitaxel

Guidance literature:: Multi-step reaction with 6 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

6: 85 percent / DMAP / CH₂Cl₂ / 1 h / Ambient temperature

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