10-Deacetylbaccatin III supplier

Name
10-Deacetylbaccatin III
EINECS 418-680-6
CAS No. 32981-86-5
Article Data28
CAS DataBase
Density 1.41 g/cm³
Solubility Insoluble in water
Melting Point 231-236 °C
Formula C₂₉H₃₆O₁₀
Boiling Point 716.8 °C at 760 mmHg
Molecular Weight 544.599
Flash Point 233.5 °C
Transport Information
Appearance white solid
Safety 45-38-36/37/39-28A
Risk Codes 23/24/25
Molecular Structure
Hazard Symbols T
Synonyms 10-DAB-III; DESACETYLBACCATINE; Docetaxel impurity E; 10-Deacetylbaccatin III; 10-DEACETYLBACCATIN; 10-Dab; 10-Deacetylbaccatin-III; 10-desacetylbaccatin III; 10-Deacetylbaccatine; 10-Deacetyl; 10-DAB (10-Deacetylbaccatin); 10DBA III; 10-deacetylbaccatin11; 查看更多英文别名收起
PSA 159.82000
LogP 1.08180

Synthetic route

: 115437-18-8
7-triethylsilyl-10-deacetylbaccatin III

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
With sodium periodate In tetrahydrofuran; water at 30 - 40℃; for 144h;	88%
With hydrogenchloride In ethanol at 0℃; for 24h;	67%
With sodium hypochlorite In acetone; acetonitrile at 20℃; for 2h;

: 27548-93-2
baccatin III

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol for 2h; Ambient temperature;	87%
With dihydrogen peroxide; calcium carbonate In tetrahydrofuran for 72h; Ambient temperature;	57%

: 33069-62-4
taxol

A: 32981-86-5
10-deacetylbaccatin III

B: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

C: 71629-92-0
10-deacetyl-7-epi-baccatin III

Conditions

Conditions	Yield
With lithium iodide In methanol for 10h; Ambient temperature;	A 58% B 82% C 40%
With lithium iodide In methanol for 10h; Ambient temperature;	A 58% B 82% C 40%

...Expand

: 33069-62-4
taxol

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol for 2h; Ambient temperature;	82%
Multi-step reaction with 2 steps 1: 81 percent / pyridine / CH2Cl2 / Ambient temperature 2: 22 percent / LiI / methanol / Ambient temperature; 2 weeks View Scheme

: 500726-11-4
7-O-chloroacetylbaccatin III

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
With water; hydrazine In ethanol at 20℃; for 2h; Product distribution / selectivity;	75%

: 32981-90-1
7-O-acetylbaccatine III

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
With water; hydrazine In ethanol at 20℃; for 2h; Product distribution / selectivity;	75%
With sodium methylate at 20℃; for 2h; Product distribution / selectivity;	75%

: 148930-54-5
(2aR,4S,4aS,6R,9S,11S,12S,12bS)-6,12b-bis(acetyloxy)-9-({(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl}oxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9, 10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

A: 32981-86-5
10-deacetylbaccatin III

B: 32981-85-4
methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

C: 71629-92-0
10-deacetyl-7-epi-baccatin III

Conditions

Conditions	Yield
With lithium iodide In methanol Ambient temperature; 2 weeks;	A 22% B 71% C 34%

...Expand

: 71629-92-0
10-deacetyl-7-epi-baccatin III

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
With Bacillus mycoides AS1.182 In acetone at 27℃; for 168h;	58.9%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In xylene at 80℃; Product distribution; C-7-epimerization under base conditions; further taxoids;

: 191276-24-1
10-dehydro-10-deacetylbaccatin III (V)

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
With sodium cyanoborohydride	56%

: 197013-82-4
7-α-glucosyloxyacetyl paclitaxel

A: 32981-86-5
10-deacetylbaccatin III

B: 71629-92-0
10-deacetyl-7-epi-baccatin III

C: 27548-93-2
baccatin III

D: 31077-81-3
7-epi-baccatine III

Conditions

Conditions	Yield
With Synechocystis sp. PCC 6803; BG-11 medium at 25℃; for 168h; Further byproducts.;	A 16% B 10% C 33% D 27%

...Expand

: 197013-82-4
7-α-glucosyloxyacetyl paclitaxel

A: 32981-86-5
10-deacetylbaccatin III

B: 33069-62-4
taxol

C: 27548-93-2
baccatin III

Conditions

Conditions	Yield
With Nicotiana tabacum at 25℃;	A 10% B 25% C 11%

...Expand

: 78432-77-6
10-deacetylpaclitaxel

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
In dichloromethane	24%

: 197013-82-4
7-α-glucosyloxyacetyl paclitaxel

A: 32981-86-5
10-deacetylbaccatin III

B: 78432-77-6
10-deacetylpaclitaxel

C: 33069-62-4
taxol

D: 105454-04-4
7-epipaclitaxel

Conditions

Conditions	Yield
With Marchantia polymorpha; BG-11 medium at 25℃; Further byproducts.;	A 8% B 10% C 17% D 8%

...Expand

: 67-56-1
methanol

: 71610-00-9
Cephalomannine

A: 31077-81-3
7-epi-baccatin III

B: 32981-86-5
10-deacetylbaccatin III

: 71610-01-0
(2R,3S)-2-Hydroxy-3-((E)-2-methyl-but-2-enoylamino)-3-phenyl-propionic acid methyl ester

D: 27548-93-2
baccatin III

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; other base; Further byproducts given;	A 4.5 mg B 4.6 mg C 6.6 mg D 4.9 mg

...Expand

: 71610-00-9
Cephalomannine

A: 31077-81-3
7-epi-baccatin III

B: 32981-86-5
10-deacetylbaccatin III

: 71610-01-0
(2R,3S)-2-Hydroxy-3-((E)-2-methyl-but-2-enoylamino)-3-phenyl-propionic acid methyl ester

D: 27548-93-2
baccatin III

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; Further byproducts given;	A 4.5 mg B 4.6 mg C 6.6 mg D 4.9 mg

...Expand

: 71610-00-9
Cephalomannine

A: 31077-81-3
7-epi-baccatin III

B: 32981-86-5
10-deacetylbaccatin III

C: 76480-33-6, 539851-34-8
(1Z,3E,9Z)-1-Chlorohexadeca-5,7-diyne-1,3,9-trien-14-ol

D: 27548-93-2
baccatin III

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; Further byproducts given;	A 4.5 mg B 4.6 mg C 6.6 mg D 4.9 mg

...Expand

: 71610-00-9
Cephalomannine

A: 32981-86-5
10-deacetylbaccatin III

: 71610-01-0
(2R,3S)-2-Hydroxy-3-((E)-2-methyl-but-2-enoylamino)-3-phenyl-propionic acid methyl ester

C: 76429-85-1
10-Deacetylcephalomannine

D: 27548-93-2
baccatin III

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; Further byproducts given;	A 4.6 mg B 6.6 mg C 1.6 mg D 4.9 mg

...Expand

: 71610-00-9
Cephalomannine

A: 32981-86-5
10-deacetylbaccatin III

: 71610-01-0
(2R,3S)-2-Hydroxy-3-((E)-2-methyl-but-2-enoylamino)-3-phenyl-propionic acid methyl ester

C: 71629-92-0
10-deacetyl-7-epi-baccatin III

D: 27548-93-2
baccatin III

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 5h; Ambient temperature; Further byproducts given;	A 4.6 mg B 6.6 mg C 3.3 mg D 4.9 mg

...Expand

: 591-51-5
phenyllithium

: 187961-12-2
C28H33Cl3O13

A: 32981-86-5
10-deacetylbaccatin III

B: 27548-93-2
baccatin III

Conditions

Conditions	Yield
In tetrahydrofuran at -78℃; Phenylation;

...Expand

: 27548-93-2
baccatin III

A: 32981-86-5
10-deacetylbaccatin III

B: 71629-92-0
10-deacetyl-7-epi-baccatin III

Conditions

Conditions	Yield
With zinc(II) chloride In methanol at 20℃;	A 15 mg B 46 mg

: 187960-83-4
C29H48O7Si

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
Multi-step reaction with 16 steps 1: 91 percent / tetrahydrofuran / -78 °C 2: 94 percent / HCl; H2O; NaI / dioxane 3: 92 percent / pyridine / CH2Cl2 / -30 °C 4: Dess-Martin periodinane / CH2Cl2 5: Et3N 6: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 7: N,N-diisopropylethylamine / 55 °C 8: NH4F / methanol / 20 °C 9: tetrahydrofuran / -78 °C 10: imidazole / CHCl3 11: 92 percent / pyridine / CH2Cl2 12: 76 percent / KCN / ethanol / 0 °C 13: 95 percent / (i-Pr)2NEt / toluene / 110 °C 14: 89 percent / DMAP 15: 96 percent / TASF / tetrahydrofuran / 0 °C 16: tetrahydrofuran / -78 °C View Scheme

Yield

Multi-step reaction with 16 steps
1: 91 percent / tetrahydrofuran / -78 °C
2: 94 percent / HCl; H2O; NaI / dioxane
3: 92 percent / pyridine / CH2Cl2 / -30 °C
4: Dess-Martin periodinane / CH2Cl2
5: Et3N
6: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C
7: N,N-diisopropylethylamine / 55 °C
8: NH4F / methanol / 20 °C
9: tetrahydrofuran / -78 °C
10: imidazole / CHCl3
11: 92 percent / pyridine / CH2Cl2
12: 76 percent / KCN / ethanol / 0 °C
13: 95 percent / (i-Pr)2NEt / toluene / 110 °C
14: 89 percent / DMAP
15: 96 percent / TASF / tetrahydrofuran / 0 °C
16: tetrahydrofuran / -78 °C
View Scheme

: 187960-85-6
((1S,5S,6R,7S,8S,9S,12S)-8,9-Dihydroxy-7,11,14,14-tetramethyl-3-oxo-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-en-6-yl)-acetaldehyde

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1: 92 percent / pyridine / CH2Cl2 / -30 °C 2: Dess-Martin periodinane / CH2Cl2 3: Et3N 4: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 5: N,N-diisopropylethylamine / 55 °C 6: NH4F / methanol / 20 °C 7: tetrahydrofuran / -78 °C 8: imidazole / CHCl3 9: 92 percent / pyridine / CH2Cl2 10: 76 percent / KCN / ethanol / 0 °C 11: 95 percent / (i-Pr)2NEt / toluene / 110 °C 12: 89 percent / DMAP 13: 96 percent / TASF / tetrahydrofuran / 0 °C 14: tetrahydrofuran / -78 °C View Scheme

Yield

Multi-step reaction with 14 steps
1: 92 percent / pyridine / CH2Cl2 / -30 °C
2: Dess-Martin periodinane / CH2Cl2
3: Et3N
4: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C
5: N,N-diisopropylethylamine / 55 °C
6: NH4F / methanol / 20 °C
7: tetrahydrofuran / -78 °C
8: imidazole / CHCl3
9: 92 percent / pyridine / CH2Cl2
10: 76 percent / KCN / ethanol / 0 °C
11: 95 percent / (i-Pr)2NEt / toluene / 110 °C
12: 89 percent / DMAP
13: 96 percent / TASF / tetrahydrofuran / 0 °C
14: tetrahydrofuran / -78 °C
View Scheme

: C31H52O7Si

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1: 94 percent / HCl; H2O; NaI / dioxane 2: 92 percent / pyridine / CH2Cl2 / -30 °C 3: Dess-Martin periodinane / CH2Cl2 4: Et3N 5: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 6: N,N-diisopropylethylamine / 55 °C 7: NH4F / methanol / 20 °C 8: tetrahydrofuran / -78 °C 9: imidazole / CHCl3 10: 92 percent / pyridine / CH2Cl2 11: 76 percent / KCN / ethanol / 0 °C 12: 95 percent / (i-Pr)2NEt / toluene / 110 °C 13: 89 percent / DMAP 14: 96 percent / TASF / tetrahydrofuran / 0 °C 15: tetrahydrofuran / -78 °C View Scheme

Yield

Multi-step reaction with 15 steps
1: 94 percent / HCl; H2O; NaI / dioxane
2: 92 percent / pyridine / CH2Cl2 / -30 °C
3: Dess-Martin periodinane / CH2Cl2
4: Et3N
5: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C
6: N,N-diisopropylethylamine / 55 °C
7: NH4F / methanol / 20 °C
8: tetrahydrofuran / -78 °C
9: imidazole / CHCl3
10: 92 percent / pyridine / CH2Cl2
11: 76 percent / KCN / ethanol / 0 °C
12: 95 percent / (i-Pr)2NEt / toluene / 110 °C
13: 89 percent / DMAP
14: 96 percent / TASF / tetrahydrofuran / 0 °C
15: tetrahydrofuran / -78 °C
View Scheme

: ((1S,5S,6R,7S,8S,12S)-7,11,14,14-Tetramethyl-3,9-dioxo-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-en-6-yl)-acetaldehyde

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: Et3N 2: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 3: N,N-diisopropylethylamine / 55 °C 4: NH4F / methanol / 20 °C 5: tetrahydrofuran / -78 °C 6: imidazole / CHCl3 7: 92 percent / pyridine / CH2Cl2 8: 76 percent / KCN / ethanol / 0 °C 9: 95 percent / (i-Pr)2NEt / toluene / 110 °C 10: 89 percent / DMAP 11: 96 percent / TASF / tetrahydrofuran / 0 °C 12: tetrahydrofuran / -78 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: Et3N
2: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C
3: N,N-diisopropylethylamine / 55 °C
4: NH4F / methanol / 20 °C
5: tetrahydrofuran / -78 °C
6: imidazole / CHCl3
7: 92 percent / pyridine / CH2Cl2
8: 76 percent / KCN / ethanol / 0 °C
9: 95 percent / (i-Pr)2NEt / toluene / 110 °C
10: 89 percent / DMAP
11: 96 percent / TASF / tetrahydrofuran / 0 °C
12: tetrahydrofuran / -78 °C
View Scheme

: 187961-05-3
((1S,5S,6R,7S,8S,9S,12S)-9-Hydroxy-7,11,14,14-tetramethyl-3-oxo-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-en-6-yl)-acetaldehyde

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: Dess-Martin periodinane / CH2Cl2 2: Et3N 3: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 4: N,N-diisopropylethylamine / 55 °C 5: NH4F / methanol / 20 °C 6: tetrahydrofuran / -78 °C 7: imidazole / CHCl3 8: 92 percent / pyridine / CH2Cl2 9: 76 percent / KCN / ethanol / 0 °C 10: 95 percent / (i-Pr)2NEt / toluene / 110 °C 11: 89 percent / DMAP 12: 96 percent / TASF / tetrahydrofuran / 0 °C 13: tetrahydrofuran / -78 °C View Scheme

Yield

Multi-step reaction with 13 steps
1: Dess-Martin periodinane / CH2Cl2
2: Et3N
3: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C
4: N,N-diisopropylethylamine / 55 °C
5: NH4F / methanol / 20 °C
6: tetrahydrofuran / -78 °C
7: imidazole / CHCl3
8: 92 percent / pyridine / CH2Cl2
9: 76 percent / KCN / ethanol / 0 °C
10: 95 percent / (i-Pr)2NEt / toluene / 110 °C
11: 89 percent / DMAP
12: 96 percent / TASF / tetrahydrofuran / 0 °C
13: tetrahydrofuran / -78 °C
View Scheme

: 187960-87-8
2-((1S,5S,6S,7S,8S,12S)-7,11,14,14-Tetramethyl-3,9-dioxo-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-en-6-yl)-propenal

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C 2: N,N-diisopropylethylamine / 55 °C 3: NH4F / methanol / 20 °C 4: tetrahydrofuran / -78 °C 5: imidazole / CHCl3 6: 92 percent / pyridine / CH2Cl2 7: 76 percent / KCN / ethanol / 0 °C 8: 95 percent / (i-Pr)2NEt / toluene / 110 °C 9: 89 percent / DMAP 10: 96 percent / TASF / tetrahydrofuran / 0 °C 11: tetrahydrofuran / -78 °C View Scheme

Yield

Multi-step reaction with 11 steps
1: 89 percent / ZnCl2 / tetrahydrofuran / -78 °C
2: N,N-diisopropylethylamine / 55 °C
3: NH4F / methanol / 20 °C
4: tetrahydrofuran / -78 °C
5: imidazole / CHCl3
6: 92 percent / pyridine / CH2Cl2
7: 76 percent / KCN / ethanol / 0 °C
8: 95 percent / (i-Pr)2NEt / toluene / 110 °C
9: 89 percent / DMAP
10: 96 percent / TASF / tetrahydrofuran / 0 °C
11: tetrahydrofuran / -78 °C
View Scheme

: 187961-09-7
(1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-8-hydroxy-7,11,14,14-tetramethyl-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-ene-3,9-dione

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: tetrahydrofuran / -78 °C 2: imidazole / CHCl3 3: 92 percent / pyridine / CH2Cl2 4: 76 percent / KCN / ethanol / 0 °C 5: 95 percent / (i-Pr)2NEt / toluene / 110 °C 6: 89 percent / DMAP 7: 96 percent / TASF / tetrahydrofuran / 0 °C 8: tetrahydrofuran / -78 °C View Scheme

: 187961-07-5
(1S,5S,6S,7S,8S,12S)-6-((R)-2-Hydroxy-1-methylene-pent-4-enyl)-7,11,14,14-tetramethyl-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.01,5]tetradec-10-ene-3,9-dione

: 32981-86-5
10-deacetylbaccatin III

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: N,N-diisopropylethylamine / 55 °C 2: NH4F / methanol / 20 °C 3: tetrahydrofuran / -78 °C 4: imidazole / CHCl3 5: 92 percent / pyridine / CH2Cl2 6: 76 percent / KCN / ethanol / 0 °C 7: 95 percent / (i-Pr)2NEt / toluene / 110 °C 8: 89 percent / DMAP 9: 96 percent / TASF / tetrahydrofuran / 0 °C 10: tetrahydrofuran / -78 °C View Scheme

: 32981-86-5
10-deacetylbaccatin III

: 994-30-9
triethylsilyl chloride

: 115437-18-8
7-triethylsilyl-10-deacetylbaccatin III

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide	100%
With pyridine Ambient temperature;	98%
In pyridine at 25℃; for 24h;	97.7%

: 32981-86-5
10-deacetylbaccatin III

: 158660-66-3
10-deacetyl-2-(hexahydro)baccatin III

Conditions

Conditions	Yield
With hydrogen; Rh on carbon In methanol at 35℃; under 25857.4 Torr; for 24h;	100%

: 32981-86-5
10-deacetylbaccatin III

: 506-96-7
Acetyl bromide

: 76-02-8
Trichloroacetyl chloride

: 204124-97-0
7-trichloroacetylbaccatin III

Conditions

Conditions	Yield
Stage #1: 10-deacetylbaccatin III; trifluoroacetyl chloride With pyridine In chloroform at 35℃; for 4h; Stage #2: Acetyl bromide In chloroform at 20℃; for 5h;	100%
Stage #1: 10-deacetylbaccatin III; trifluoroacetyl chloride With pyridine In chloroform at 35℃; for 4h; Stage #2: Acetyl bromide In chloroform at 20℃; for 5h;	100%

...Expand

: 32981-86-5
10-deacetylbaccatin III

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: 95603-44-4
7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III

Conditions

Conditions	Yield
With pyridine In dichloromethane at 50℃; under 7500.75 Torr; for 0.0277778h; Concentration; Temperature; Pressure;	98.4%
With pyridine In dichloromethane at 2℃; for 2h; Temperature;	98.9%
With pyridine at 0 - 20℃;	91%

: 32981-86-5
10-deacetylbaccatin III

: 108-24-7
acetic anhydride

: 27548-93-2
baccatin III

Conditions

Conditions	Yield
lanthanum(lll) triflate In tetrahydrofuran for 2h;	97%
With cerium(III) chloride heptahydrate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Cooling with ice;	96%
With cerium(III) chloride heptahydrate In tetrahydrofuran at 20℃; for 2h;	94.4%

: 32981-86-5
10-deacetylbaccatin III

: 108-24-7
acetic anhydride

: 92950-44-2
7,13-diacetyl baccatin III

Conditions

Conditions	Yield
With dmap In pyridine at 23℃; for 20h; Inert atmosphere;	96%
In pyridine at 80℃; for 24h;	30 mg

: 32981-86-5
10-deacetylbaccatin III

: 994-30-9
triethylsilyl chloride

: 194720-19-9
7,10,13-tris(triethylsilyl)-10-deacetylbaccatin III

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 40h; silylation;	96%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 47h; silylation;	96%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	96%

: 32981-86-5
10-deacetylbaccatin III

: 97-72-3
2-Methylpropionic anhydride

: 207680-02-2
10-isobutyloyl 10-deacetylbaccatin III

Conditions

Conditions	Yield
lanthanum(lll) triflate In tetrahydrofuran	96%
With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In tetrahydrofuran; chloroform at -40℃; for 48h;	89%
With cerium(III) chloride In tetrahydrofuran at 20℃; for 4h;

: 32981-86-5
10-deacetylbaccatin III

: 501-53-1
benzyl chloroformate

: 194864-02-3
C-7,C-10-dibenzyloxycarbonyl-10-deacetyl baccatin III

Conditions

Conditions	Yield
With dmap In tetrahydrofuran at 40 - 50℃;	96%
With dmap In tetrahydrofuran at 40 - 60℃; for 1.5h;	81%
With n-hexyllithium In tetrahydrofuran at -44 - 40℃;

: 32981-86-5
10-deacetylbaccatin III

: 191276-24-1
10-dehydro-10-deacetylbaccatin III (V)

Conditions

Conditions	Yield
With copper diacetate In methanol	95%

: 32981-86-5
10-deacetylbaccatin III

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 184586-78-5
(1S,2S,3R,4S,5R,7S,8S,10R,13S)-4-acetoxy-2-benzoyloxy-5,20-epoxy-10-formyloxy-9-oxo-1,7,13-trihydroxytax-11-ene

Conditions

Conditions	Yield
With dmap; trifluoromethylsulfonic anhydride at 0℃;	95%
With dmap; trifluoromethylsulfonic anhydride for 0.166667h;	95%
With pyridine; trifluoromethylsulfonic anhydride; water 1.) -20 deg C, 10 min; 2.) 0 deg C, 3 h; Yield given. Multistep reaction;

: 32981-86-5
10-deacetylbaccatin III

: 79-04-9
chloroacetyl chloride

: 500726-10-3
7,10-di-O-chloroacetyl-10-deacetylbaccatin III

Conditions

Conditions	Yield
With pyridine; dmap In dichloromethane at 25 - 30℃; for 0.5h;	95%
Stage #1: 10-deacetylbaccatin III With pyridine; dmap In dichloromethane for 0.166667h; Stage #2: chloroacetyl chloride In dichloromethane at 25 - 30℃; for 0.333333h;	95%
With pyridine; dmap In dichloromethane at -5 - 5℃; for 2h; Inert atmosphere;
Stage #1: 10-deacetylbaccatin III With pyridine; dmap In dichloromethane for 0.166667h; Stage #2: chloroacetyl chloride In dichloromethane at 5 - 10℃; for 2h;

: 32981-86-5
10-deacetylbaccatin III

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

: 1353716-43-4
7,10,13-tri-Boc-10-deacetylbaccatin

Conditions

Conditions	Yield
With dmap In tetrahydrofuran; dichloromethane at 20℃; for 12h; Inert atmosphere;	95%

: 32981-86-5
10-deacetylbaccatin III

: 207680-13-5
N,O-bis(triethylsilyl) trifluoroacetamide

: 10-deacetyl-10-triethylsiloxybaccatin III

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 0℃; for 0.0833333h; Inert atmosphere;	95%

: N,O-bis-trimethylsilyl-trifluoromethyl-acetamide

: 32981-86-5
10-deacetylbaccatin III

: 207680-14-6
10-trimethylsilyl-10-deacetyl baccatin III

Conditions

Conditions	Yield
Stage #1: N,O-bis-trimethylsilyl-trifluoromethyl-acetamide; 10-deacetylbaccatin III In tetrahydrofuran at 25℃; Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran for 0.416667h;	93%

: 32981-86-5
10-deacetylbaccatin III

: 99-33-2
3,5-dinitrobenoyl chloride

A: 1033517-17-7
7,10-(di-3',5'-dinitrobenzoyl)-10-deacetylbaccatin III

B: 1033517-21-3
10-(3',5'-dinitrobenzoyl)-10-deacetylbaccatin III

C: 1033517-19-9
7-(3',5'-dinitrobenzoyl)-10-deacetylbaccatin III

D: 1033517-23-5
7,10,13-(tri-3',5'-dinitrobenzoyl)-10-deacetylbaccatin III

Conditions

Conditions	Yield
With pyridine In chloroform at 38 - 42℃;	A 93% B n/a C n/a D 0.9%

...Expand

: 32981-86-5
10-deacetylbaccatin III

: (2aR,4S,4aS,8R,11S,12S,12aR,12bS,Z)-12b-acetoxy-4,11-dihydroxy-4a,8,13,13-tetramethyl-5,9-dioxo-2a,3,4,4a,5,8,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Conditions

Conditions	Yield
With diethylamino-sulfur trifluoride In tetrahydrofuran at -78℃; for 3h; Molecular sieve; Inert atmosphere;	93%

: 32981-86-5
10-deacetylbaccatin III

: 21947-71-7
cinnamic anhydride

: 10-O-cinnamoyl-10-deacetylbaccatin III

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In tetrahydrofuran; chloroform at -20℃; for 72h;	93%

: 32981-86-5
10-deacetylbaccatin III

: 92950-42-0
13-dehydro-10-deacetylbaccatin III

Conditions

Conditions	Yield
With ozone In methanol; dichloromethane at -78℃; for 0.583333h;	92%
With pyridinium chlorochromate In dichloromethane for 0.75h; Ambient temperature;	79%
With periodic acid In 1,4-dioxane for 72h; Ambient temperature;	75%
With 3-chloro-benzenecarboperoxoic acid In ethyl acetate for 24h; Ambient temperature;

: 32981-86-5
10-deacetylbaccatin III

: 108-24-7
acetic anhydride

: 32981-90-1
7-O-acetylbaccatine III

Conditions

Conditions	Yield
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In tetrahydrofuran at 10℃; for 1h; Reagent/catalyst; Solvent; Temperature; Concentration; Inert atmosphere;	91.8%

: 32981-86-5
10-deacetylbaccatin III

: 92950-45-3
10-dehydro 10-deacetyl 7-epibaccatin V

Conditions

Conditions	Yield
With triethylamine; copper dichloride In ethanol; ethyl acetate at -13 - -1.3℃; for 1h;	91.3%
Stage #1: 10-deacetylbaccatin III With triethylamine; copper dichloride In ethanol; ethyl acetate at -17.6 - -1.3℃; for 1h; Stage #2: With trifluoroacetic acid In ethanol; ethyl acetate for 0.25h; Product distribution / selectivity;
Stage #1: 10-deacetylbaccatin III With triethylamine; copper dichloride In ethanol; ethyl acetate at -13 - -1.3℃; Inert atmosphere; Stage #2: With trifluoroacetic acid In ethanol; ethyl acetate for 0.25h;
With triethylamine; copper dichloride In ethanol; ethyl acetate at -13℃; for 1h; Inert atmosphere;
Stage #1: 10-deacetylbaccatin III With triethylamine; copper dichloride In ethanol; ethyl acetate at -13 - -1.3℃; for 1h; Stage #2: With trifluoroacetic acid In ethanol; ethyl acetate for 0.25h;

: 32981-86-5
10-deacetylbaccatin III

: 18162-48-6
tert-butyldimethylsilyl chloride

: 115437-18-8
7-triethylsilyl-10-deacetylbaccatin III

Conditions

Conditions	Yield
With pyridine at 25℃; for 17h;	91%

: 32981-86-5
10-deacetylbaccatin III

: 93-97-0
benzoic acid anhydride

: 207680-03-3
10-O-benzoyl-10-deacetylbaccatin III

Conditions

Conditions	Yield
lanthanum(lll) triflate In tetrahydrofuran	91%
With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In tetrahydrofuran; chloroform at -20℃; for 168h;	84%
With cerium(III) chloride In tetrahydrofuran at 20℃; for 4h;

: 32981-86-5
10-deacetylbaccatin III

: 13154-24-0
triisopropylsilyl chloride

: C38H56O10Si

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 23h;	90.8%

: 32981-86-5
10-deacetylbaccatin III

: 98-59-9
p-toluenesulfonyl chloride

: C43H48O14S2

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 4h;	90%

: 32981-86-5
10-deacetylbaccatin III

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: C31H37Cl3O10

Conditions

Conditions	Yield
With pyridine In dichloromethane at 35℃; for 27h;	89.7%

: 32981-86-5
10-deacetylbaccatin III

: 616-38-6
carbonic acid dimethyl ester

: 183133-94-0
4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene

Conditions

Conditions	Yield
With dmap; caesium bromide; sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at -30℃; for 3h; Temperature; Reagent/catalyst;	89.6%

: 32981-86-5
10-deacetylbaccatin III

: 994-30-9
triethylsilyl chloride

: 149107-84-6
7,10-bis(triethylsilyl)-10-deacetylbaccatin III

Conditions

Conditions	Yield
Stage #1: 10-deacetylbaccatin III; triethylsilyl chloride With dmap; triethylamine In tetrahydrofuran at 25℃; Inert atmosphere; Stage #2: With lithium bromide In tetrahydrofuran at 20 - 70℃; Inert atmosphere;	89%
Stage #1: 10-deacetylbaccatin III; triethylsilyl chloride With dmap; triethylamine In tetrahydrofuran at 20℃; for 5.5h; Inert atmosphere; Stage #2: With lithium bromide In tetrahydrofuran at 65 - 70℃; for 7h;	84%
Stage #1: 10-deacetylbaccatin III; triethylsilyl chloride With dmap; triethylamine In tetrahydrofuran at 20℃; for 5.5h; Inert atmosphere; Stage #2: With lithium bromide In tetrahydrofuran at 65 - 70℃; for 7h;	84%

10-Deacetylbaccatin III Specification

10-Deacetylbaccatin III is a natural organic compound isolated from the bark of the Pacific yew tree (Taxus brevifolia) and related species. With the CAS Number 32981-86-5, it is also called DESACETYLBACCATINE; BACCATIN III, 10-DEACETYL-; 10-O-DEACETYLBACCATIN III; 10-DAB-III; 10-DEACETYLBACCATIN; 10-deacetylbaccatiniii(extaxusbaccata). 10-Deacetylbaccatin III is used as a chemical intermediate in the preparation of the anti-cancer drug paclitaxel.

Physical properties about 10-Deacetylbaccatin III are: (1)ACD/LogP: 0.156; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 0.16; (4)ACD/LogD (pH 7.4): 0.16; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 28.98; (8)ACD/KOC (pH 7.4): 28.98; (9)#H bond acceptors: 10; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 9; (12)Index of Refraction: 1.624; (13)Molar Refractivity: 136.153 cm³; (14)Molar Volume: 385.577 cm³; (15)Polarizability: 53.975 10-24cm³; (16)Surface Tension: 67.4349975585938 dyne/cm; (17)Density: 1.412 g/cm³; (18)Flash Point: 233.452 °C; (19)Enthalpy of Vaporization: 109.981 kJ/mol; (20)Boiling Point: 716.838 °C at 760 mmHg

When you are using 10-Deacetylbaccatin III, please be cautious about it as the following:
1. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
2. In case of insufficient ventilation, wear suitable respiratory equipment;
3. Wear suitable protective clothing, gloves and eye/face protection;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C29H36O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,21-22,24,31-33,36H,11-13H2,1-5H3/t17-,18-,19+,21+,22-,24-,27+,28-,29+/m0/s1;
(2)InChIKey=YWLXLRUDGLRYDR-ZHPRIASZSA-N;
(3)SmilesO1[C@H]2[C@@](C1)([C@@H]1[C@@]([C@H](C2)O)(C([C@@H](C2=C([C@H](C[C@@]([C@H]1OC(c1ccccc1)=O)(C2(C)C)O)O)C)O)=O)C)OC(=O)C

Product Name

10-Deacetylbaccatin III

Synthetic route

10-Deacetylbaccatin III Specification

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