7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]

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Chemical Name:7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]
CAS No.:382596-29-4
Molecular Formula:C₆₃H₇₁NO₁₈
Molecular Weight:1130.25
Hs Code.:

Synonyms:7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]

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Chemical Property of 7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]

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Technology Process of 7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]

There total 7 articles about 7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate] 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: 90.0%

: 382596-28-3
(4S,5R)-4-[4-(benzyloxy)phenyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylic acid

: 7-O-benzyloxycarbonylbaccatin III

: 382596-29-4
7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In toluene; at 90 ℃; for 1.5h;
DOI:10.1021/jo0102516

Reference yield:

: 4397-53-9
p-benzyloxybenzaldehyde

: 382596-29-4
7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / CH₂Cl₂ / 24 h / 20 °C

2.1: K₂[OsO₂(OH)4]; LiOH*H₂O; (DHQ)2PHAL / 2-methyl-propan-2-ol; H₂O; acetonitrile / 24 h / 0 - 5 °C

2.2: HCl / ethanol / 4 h / 90 °C

3.1: 23 g / NaHCO₃ / tetrahydrofuran / 5 h / 20 °C

4.1: 75 percent / PPTS / toluene / 8 h / 90 °C

5.1: LiOH*H₂O / tetrahydrofuran; methanol / 2 h / 22 °C

6.1: 90 percent / DCC; DMAP / toluene / 1.5 h / 90 °C

With dmap; lithium hydroxide; Hydroquinone 1,4-phthalazinediyl diether; K2; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 1.1: Wittig olefination / 2.1: Sharpless aminohydroxylation;
DOI:10.1021/jo0102516

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 382596-29-4
7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]

Guidance literature:: Multi-step reaction with 4 steps

1: 23 g / NaHCO₃ / tetrahydrofuran / 5 h / 20 °C

2: 75 percent / PPTS / toluene / 8 h / 90 °C

3: LiOH*H₂O / tetrahydrofuran; methanol / 2 h / 22 °C

4: 90 percent / DCC; DMAP / toluene / 1.5 h / 90 °C

With dmap; lithium hydroxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; toluene;
DOI:10.1021/jo0102516