155396-69-3

Usage

InChI:InChI=1/C22H25NO6/c1-22(2,3)29-21(26)23-17(14-8-6-5-7-9-14)18(20(24)25)28-19(23)15-10-12-16(27-4)13-11-15/h5-13,17-19H,1-4H3,(H,24,25)/t17-,18+,19+/m0/s1

Synthetic route

(2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester (155396-68-2) → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran; water 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h;	100%

(2R,4S,5R)-3-t-butoxycarbonyl-4-phenyl-2-(4-methoxyphenyl)-5-methoxycarbonyl-1,3-oxazolidine (153652-73-4) → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
With KOH (or LiOH*H2O) In methanol; water Yield given;

tert-butyl carbamate (4248-19-5) + ammonium salt of/the/ tert-butylsulfuric acid → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 68 percent / HCOOH / methanol; H2O / 21 h / 20 °C 2: 100 percent / K2CO3 / tetrahydrofuran / 12 h / Heating 3: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min 4: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C 5: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h View Scheme

benzaldehyde (100-52-7) + sodium cyanate → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 68 percent / HCOOH / methanol; H2O / 21 h / 20 °C 2: 100 percent / K2CO3 / tetrahydrofuran / 12 h / Heating 3: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min 4: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C 5: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h View Scheme

benzaldehyde N-boc imine (150884-50-7) → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min 2: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C 3: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h View Scheme

tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate (155396-71-7) → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / K2CO3 / tetrahydrofuran / 12 h / Heating 2: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min 3: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C 4: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h View Scheme

[(1S,2R)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-(4-methoxy-benzyloxy)-3-oxo-1-phenyl-propyl]-carbamic acid tert-butyl ester (155396-67-1) → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C 2: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h View Scheme

2-(4'-methoxybenzyloxy)acetyl chloride → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 86 percent / NaH / toluene / 1.) 20 deg C, 30 min, 2.) 20 deg C, 3 h 2: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min 3: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C 4: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h View Scheme

N-<<(p-Methoxybenzyl)oxy>acetyl>-2,10-camphorsultam (155396-70-6) → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min 2: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C 3: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h View Scheme

p-Anisaldehyde dimethyl acetal (2186-92-7) → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / PPTS / toluene / 0.5 h / Heating 2: KOH (or LiOH*H2O) / methanol; H2O View Scheme

methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate (124605-42-1) → (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / PPTS / toluene / 0.5 h / Heating 2: KOH (or LiOH*H2O) / methanol; H2O View Scheme

7,10-(di-3',5'-dinitrobenzoyl)-10-deacetylbaccatin III (1033517-17-7) + (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) → (2R,4S,5R)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carbonyl 7,10-(di-3'',5''-dinitrobenzoyl)-10-deacetylbaccatin III (1033517-35-9)

Conditions	Yield
Stage #1: 7,10-(di-3',5'-dinitrobenzoyl)-10-deacetylbaccatin III; (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid; dmap In ethyl acetate at 40℃; Stage #2: With dicyclohexyl-carbodiimide In ethyl acetate for 0.5h;	100%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + C48H71NO9Si2 (194720-30-4) → C70H94N2O14Si2 (194720-31-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene for 0.666667h; Ambient temperature;	99%

7,10-di-O-1,3-benzodithiolan-2-yl-10-DAB (1432613-35-8) + (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) → (2α,5β,7β,10β,13α)-4-acetoxy-13-{(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxy}-1-hydroxy-7,10-di-O-1,3-benzodithiolan-2-yl-9-oxo-5,20-epoxy-tax-11-en-2-yl benzoate (1432613-38-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 18h;	96%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (646502-73-0) → 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester (646502-75-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 0.333333h;	93%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + C41H64O9Si2 (285118-36-7) → C63H87NO14Si2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; Etherification;	92%

4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene (183133-94-0) + (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) → 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-11-taxene-13α-yl (2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate (183133-95-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 2h;	91%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran
With dmap; dicyclohexyl-carbodiimide In toluene at 20 - 30℃;
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 3h;

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + C38H54O12Si → C60H77NO17Si (162888-60-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 1.5h;	89%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + 7,10-di(triethylsilyl)-5(20)-deoxy-5(20)-sulfanyl-10-deacetylbaccatin III (358621-67-7) → 5(20)-deoxy-5(20)-sulfanyl-7,10-di(triethylsilyl)-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]-10-deacetylbaccatin III (358621-68-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 1.5h;	85%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + 7-deoxy-5(20)-deoxy-5(20)-sulfanylbaccatin III (358621-71-3) → 5(20)-deoxy-5(20)-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III (1054734-45-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 80℃; for 3h;	78%

4,10-bis(deacetyl)-7-(triethylsily)baccatin III (144654-43-3) + (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) → C55H71NO14Si

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 60℃;	76%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + C27H38O9 (189097-93-6) → C49H61NO14

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 14.5h; Esterification;	65%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + C33H50O9Si (175444-20-9) → C55H73NO14Si (175444-23-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 60℃;	62%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + brevifoliol → C45H57NO13 (1048656-61-6) + C45H57NO13 (1048656-60-5) + C59H74N2O17 (1048656-62-7)

Conditions	Yield
Stage #1: (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid; brevifoliol With dmap; dicyclohexyl-carbodiimide In toluene at 25℃; for 1h; Stage #2: With methanol; toluene-4-sulfonic acid at 25℃; for 2h; Further stages.;	A 30% B 60% C 10%

Benzoic acid (1S,2S,3R,4R,7S,8S,10R,13S)-4,10-diacetoxy-1,13-dihydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (892859-27-7) + (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) → 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4,10-diacetoxy-2-benzoyloxy-1-hydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester (892859-28-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 70℃; for 10h;	54%

Benzoic acid (1S,2S,3R,4R,7S,8S,10R,13S)-4-acetoxy-1,10,13-trihydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (892859-32-4) + (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) → C79H96N2O20Si

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 2.5h;	49%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + C28H42O8 (189097-70-9) → C50H65NO13

Conditions	Yield
With 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; dicyclohexyl-carbodiimide In toluene Esterification; Heating;	44%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + 7,10-Bis<(2,2,2-trichloroethoxy)carbonyl>-10-desacetylbaccatin III → C57H61Cl6NO17 (1054786-40-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 25℃; for 2h;

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + Acetic acid (Z)-(2R,9S,11S)-9-(tert-butyl-dimethyl-silanyloxy)-11-hydroxy-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl ester → (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2R,9S,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl ester + (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11R)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl ester

Conditions	Yield
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide 1.) toluene, 21 deg C, 30 min, 2.) MeOH, 21 deg C, 1.5 h; Yield given. Multistep reaction. Yields of byproduct given;

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + Acetic acid (Z)-(2R,9S,11S)-9-(tert-butyl-dimethyl-silanyloxy)-11-hydroxy-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl ester → (2R,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-[(Z)-(2R,9S,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl] ester 3-tert-butyl ester + (2R,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-[(Z)-(2S,9R,11R)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl] ester 3-tert-butyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 21℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + Acetic acid (Z)-(2R,9S,11R)-9-(tert-butyl-dimethyl-silanyloxy)-11-hydroxy-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl ester → (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2R,9S,11R)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl ester + (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl ester (213924-94-8)

Conditions	Yield
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide 1.) toluene, 21 deg C, 30 min, 2.) MeOH, 21 deg C, 1.5 h; Yield given. Multistep reaction. Yields of byproduct given;

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + Acetic acid (Z)-(2R,9S,11R)-9-(tert-butyl-dimethyl-silanyloxy)-11-hydroxy-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl ester → (2R,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-[(Z)-(2R,9S,11R)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl] ester 3-tert-butyl ester + (2R,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-[(Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl] ester 3-tert-butyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 21℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) → 4-deacetyldocetaxel

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / DCC, DMAP / toluene / 60 °C 2: 41 percent / APTS / methanol / Ambient temperature View Scheme

Upstream product

• 153652-73-4 (2R,4S,5R)-3-t-butoxycarbonyl-4-phenyl-2-(4-methoxyphenyl)-5-methoxycarbonyl-1,3-oxazolidine 
• 155396-68-2 (2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 4248-19-5 tert-butyl carbazate 
• 100-52-7 benzaldehyde 
• 150884-50-7 benzaldehyde N-boc imine 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 155396-67-1 [(1S,2R)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-methoxy-benzyloxy)-3-oxo-1-phenyl-propyl]-carbamic acid tert-butyl ester 
• 155396-70-6 N-<<(p-Methoxybenzyl)oxy>acetyl>-2,10-camphorsultam 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 

Downstream Products

• 175444-23-2 C₅₅H₇₃NO₁₄Si 
• 194720-31-5 C₇₀H₉₄N₂O₁₄Si₂ 
• 213924-94-8 (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1⁽¹²⁾,5-diene-3,7-diyn-11-yl ester 
• 1054734-45-0 5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-7-deoxy-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]baccatin III 
• 358621-68-8 5⁽²⁰⁾-deoxy-5⁽²⁰⁾-sulfanyl-7,10-di(triethylsilyl)-13-[[(4S,5R)-2-(4-methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]-10-deacetylbaccatin III 
• 646502-75-2 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester 
• 1048656-61-6 C₄₅H₅₇NO₁₃ 
• 1048656-60-5 C₄₅H₅₇NO₁₃ 
• 1048656-62-7 C₅₉H₇₄N₂O₁₇ 
• 183133-95-1 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-11-taxene-13α-yl (2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate 
• 1432613-38-1 (2α,5β,7β,10β,13α)-4-acetoxy-13-{(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxy}-1-hydroxy-7,10-di-O-1,3-benzodithiolan-2-yl-9-oxo-5,20-epoxy-tax-11-en-2-yl benzoate 
• 1033517-35-9 (2R,4S,5R)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carbonyl 7,10-(di-3'',5''-dinitrobenzoyl)-10-deacetylbaccatin III 

Relevant academic research and scientific papers

Process for preparing taxane derivatives

Method of preparing taxane derivatives of general formula (I) by esterification of protected baccatine III or 10-deacetyl-baccatine III by means of an acid of general formula (VII), deprotection of the side chain and elimination of the hydroxy function protection groupings. In general formulae (I) and (VII): Ar stands for aryl, R is hydrogen or acetyl, R1 is benzoyl or R2 --O--CO-- in which R2 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, phenyl or heterocyclyl, and R3 is hydrogen, alkoxy, optionally substituted aryl. STR1

2-Monosubstituted-1,3-Oxazolidines as Improved Protective Groups of N-Boc-Phenylisoserine in Docetaxel Preparation

A new route for semisynthetic docetaxel, 1, is desribed using 2-monosubstituted-4-phenyl-1,3-oxazolidine-5-carboxylic acids in esterification of 7,10-O-diTroc-10-desacetylbaccatin III (4).Subsequent deprotection of esters 10(+10') afforded title compound 1 without removal of the Boc group.

Highly stereocontrolled and efficient preparation of the protected, esterification-ready docetaxel (Taxotere) side chain

A high-yield synthesis of the p-methoxybenzylidene-protected docetaxel (Taxotere) side chain, a useful derivative for efficient, epimerization-free esterification of the 7,10-bis[(trichloroethoxy)carbonyl] derivative of 10-desacetylbaccatin III for the preparation of docetaxel, has been effected; the C-4 and C-5 stereocenters of the 1,3-oxazolidine are generated with complete (≥99%) stereocontrol whereas that at C-2 is produced with 96% selectivity.