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24512-63-8

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24512-63-8 Usage

Pharmacological effects

Geniposide, also known as Gardenia glycosides, geniposide. It is a brown to white crystalline powder, with little flavor and no bitter taste, a cycloolefin ether glycoside compound extracted from the dry and ripe fruit of Rubiaceae Gardenia. Geniposide has a significant role in promoting bile secretion, and can reduce blood bilirubin, as well as promote rapid excretion of bilirubin in the blood. It has an inhibitory effect on Streptococcus hemolyticus and skin fungi. It also has antipyretic, analgesic, sedative, antihypertensive and hemostatic effects. Geniposide has the function of purging pathogenic fire and eliminating restlessness, clearing heat and eliminating damp, decreasing swellinging to relieving pain. The Indications of Geniposide are heat disease, dysphoria, coma delirium, jaundice, heat stranguria, heat in blood, swelling and pain of eye, pathopyretic ulcer, and sprain.

Chemical Properties

White powder

Uses

Geniposide is an iridoid glycoside isolated from the fruit of Gardenia jasminoides Ellis. Geniposide is one of the biologically active ingredients of gardenia fruit. Geniposide is widely used in multi-component injection in the treatment of cerebrovascula

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Geniposide is an iridoid glycoside with a variety of biological activities including neuroprotective, anti-diabetic, antiproliferative, and antioxidative activity. Geniposide has been shown to regulate Nrf2 translocation and upregulate downstream antioxidant protein HO-1 expression through the PI3K/Akt signaling pathway, which may account for its neuroprotective and antioxidative activity. Glucagon-like peptide 1 (GLP-1) receptor may also play a critical role in geniposide induced HO-1 expression.

Check Digit Verification of cas no

The CAS Registry Mumber 24512-63-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,5,1 and 2 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 24512-63:
(7*2)+(6*4)+(5*5)+(4*1)+(3*2)+(2*6)+(1*3)=88
88 % 10 = 8
So 24512-63-8 is a valid CAS Registry Number.

24512-63-8 Well-known Company Product Price

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  • TCI America

  • (G0385)  Geniposide  >95.0%(HPLC)

  • 24512-63-8

  • 100mg

  • 490.00CNY

  • Detail
  • TCI America

  • (G0385)  Geniposide  >95.0%(HPLC)

  • 24512-63-8

  • 1g

  • 1,990.00CNY

  • Detail
  • Sigma

  • (SML0153)  Geniposide  ≥98% (HPLC)

  • 24512-63-8

  • SML0153-10MG

  • 1,955.07CNY

  • Detail
  • Sigma

  • (SML0153)  Geniposide  ≥98% (HPLC)

  • 24512-63-8

  • SML0153-50MG

  • 7,686.90CNY

  • Detail

24512-63-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Geniposide

1.2 Other means of identification

Product number -
Other names Olea europaea L

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:24512-63-8 SDS

24512-63-8Synthetic route

geniposidic acid
27741-01-1

geniposidic acid

geniposide
24512-63-8

geniposide

10-O-(5-phenyl-2,4-pentadienoyl)-geniposide

10-O-(5-phenyl-2,4-pentadienoyl)-geniposide

A

geniposide
24512-63-8

geniposide

Conditions
ConditionsYield
With water In methanol for 1h; Ambient temperature;
geniposidic acid
27741-01-1

geniposidic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

geniposide
24512-63-8

geniposide

Conditions
ConditionsYield
In methanol; hexane; chloroform at 20℃; for 1.5h; Inert atmosphere;18.4 mg
methyl (1R,4aS,7aS)-1-Hydroxy-7-((pivaloyloxy)-methyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

methyl (1R,4aS,7aS)-1-Hydroxy-7-((pivaloyloxy)-methyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

geniposide
24512-63-8

geniposide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3.5 h / -30 - 20 °C / Molecular sieve; Inert atmosphere
2: sodium methylate / methanol / 3 h / 50 °C
View Scheme
7-(2,2-dimethyl-propionyloxymethyl)-1-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
1141938-70-6

7-(2,2-dimethyl-propionyloxymethyl)-1-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

geniposide
24512-63-8

geniposide

Conditions
ConditionsYield
With sodium methylate In methanol at 50℃; for 3h;
Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3.5 h / -30 - 20 °C / Molecular sieve; Inert atmosphere
3: sodium methylate / methanol / 3 h / 50 °C
View Scheme
O-[(α-D-mannopyranosyl)-(1->6)-(α-D-mannopyranosyl)-(1->3)-β-D-mannopyranosyl]-(1->4)-(1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-methyloxazoline
861695-58-1

O-[(α-D-mannopyranosyl)-(1->6)-(α-D-mannopyranosyl)-(1->3)-β-D-mannopyranosyl]-(1->4)-(1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-methyloxazoline

geniposide
24512-63-8

geniposide

C43H67NO30
1093135-91-1

C43H67NO30

Conditions
ConditionsYield
With endo-β-N-acetylglucosaminidase from Arthrobactor protophormiae In dimethyl sulfoxide at 23℃; for 2h; pH=7.0; aq. phosphate buffer; Enzymatic reaction;100%
geniposide
24512-63-8

geniposide

geniposidic acid
27741-01-1

geniposidic acid

Conditions
ConditionsYield
With lithium hydroxide In methanol at 50℃;90%
With sodium hydroxide at 60℃; for 1h;
With water; sodium hydroxide at 60℃; for 1.5h; Concentration;
With sodium hydroxide at 60℃; for 2h;
Conditions
ConditionsYield
With water In dichloromethane at 37℃; for 24h; Enzymatic reaction;84%
With immobilized β-glucosidase In ethyl acetate at 55℃; pH=4.5; aq. acetate buffer;63.08%
With acetate buffer; β-glucosidase at 37℃; for 5h; pH=5.0;0.5 g
geniposide
24512-63-8

geniposide

benzyl bromide
100-39-0

benzyl bromide

7-benzyl-1-(3,4,5,6-tetrabenzyl)geniposide

7-benzyl-1-(3,4,5,6-tetrabenzyl)geniposide

Conditions
ConditionsYield
Stage #1: geniposide With sodium hydride In N,N-dimethyl-formamide; mineral oil for 1h; Cooling with ice;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃;
70%
Stage #1: geniposide With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃;
42%
Stage #1: geniposide With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃;
42%
geniposide
24512-63-8

geniposide

2-Methoxypropene
116-11-0

2-Methoxypropene

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

A

4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide
256221-80-4

4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

B

2',3':4',6'-di-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide
256221-82-6

2',3':4',6'-di-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

Conditions
ConditionsYield
Stage #1: geniposide; 2,2-dimethoxy-propane With pyridinium p-toluenesulfonate In acetone at 20 - 50℃; Substitution;
Stage #2: 2-Methoxypropene In acetone at 20 - 50℃; Substitution;
A 55%
B 22%
geniposide
24512-63-8

geniposide

trityl chloride
76-83-5

trityl chloride

A

(1S,4aS,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

(1S,4aS,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

B

(1S,4aS,7aS)-1-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-7-trityloxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
265096-97-7

(1S,4aS,7aS)-1-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-7-trityloxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions
ConditionsYield
With pyridine at 20℃; tritylation;A 14%
B 37%
Conditions
ConditionsYield
With β-glucosidase In water at 37℃; for 2h;
geniposide
24512-63-8

geniposide

(1S,4aS,7aS)-1-[(S)-2-Hydroxy-1-(2-hydroxy-1-hydroxymethyl-ethoxy)-ethoxy]-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

(1S,4aS,7aS)-1-[(S)-2-Hydroxy-1-(2-hydroxy-1-hydroxymethyl-ethoxy)-ethoxy]-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate; sodium periodate 1.) RT, 2 h, 2.) RT, 2 h; Multistep reaction;
geniposide
24512-63-8

geniposide

10-deoxygeniposide
52584-79-9

10-deoxygeniposide

Conditions
ConditionsYield
With perchloric acid; hydrogen; palladium on activated charcoal In methanol312.3 mg
geniposide
24512-63-8

geniposide

acetic anhydride
108-24-7

acetic anhydride

geniposide penta-acetate
49776-64-9

geniposide penta-acetate

Conditions
ConditionsYield
In pyridine Ambient temperature;
geniposide
24512-63-8

geniposide

benzaldehyde
100-52-7

benzaldehyde

4',6'-O-benzylidene-geniposide
78924-52-4

4',6'-O-benzylidene-geniposide

Conditions
ConditionsYield
With zinc(II) chloride Ambient temperature;26.26 g
geniposide
24512-63-8

geniposide

A

C17H25(2)HO10

C17H25(2)HO10

B

C17H25(2)HO10

C17H25(2)HO10

Conditions
ConditionsYield
With triethylamine; deuterium; palladium on activated charcoal Reduction; Title compound not separated from byproducts;
geniposide
24512-63-8

geniposide

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

A

4',6'-O-isopropylidene-geniposide

4',6'-O-isopropylidene-geniposide

B

2',3':4',6'-di-O-isopropylidene-geniposide

2',3':4',6'-di-O-isopropylidene-geniposide

C

4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide
256221-80-4

4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

D

10,6'-di-O-(1-methoxy-1-methylethyl)-geniposide

10,6'-di-O-(1-methoxy-1-methylethyl)-geniposide

E

2',3':4',6'-di-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

2',3':4',6'-di-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In acetone at 20℃; for 36h; Substitution;A n/a
B 0.17 g
C 8.08 g
D 0.35 g
E n/a
geniposide
24512-63-8

geniposide

geniposidic acid aglucone

geniposidic acid aglucone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / 1 h / 60 °C
2: cellulase / H2O / 18 h / 50 °C / pH 4.0
View Scheme
geniposide
24512-63-8

geniposide

(1S,4aS,7R,7aS)-7-Acetoxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
42830-28-4

(1S,4aS,7R,7aS)-7-Acetoxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 37 percent / pyridine / 20 °C
2: 16.0 mg / pyridine
3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C
4: 50 percent / H2 / PtP2 / ethanol / 20 °C
5: 88 percent / pyridine
View Scheme
geniposide
24512-63-8

geniposide

6,7-dihydroapodantheroside pentaacetate
42830-25-1

6,7-dihydroapodantheroside pentaacetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 37 percent / pyridine / 20 °C
2: 16.0 mg / pyridine
3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C
4: 23 percent / H2 / PtP2 / ethanol / 20 °C
5: 80 percent / pyridine
View Scheme
geniposide
24512-63-8

geniposide

(1S,4aS,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
54621-24-8

(1S,4aS,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 37 percent / pyridine / 20 °C
2: 16.0 mg / pyridine
3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C
View Scheme
geniposide
24512-63-8

geniposide

(1S,4aS,7R,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
265097-02-7

(1S,4aS,7R,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 37 percent / pyridine / 20 °C
2: 16.0 mg / pyridine
3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C
4: 50 percent / H2 / PtP2 / ethanol / 20 °C
View Scheme
geniposide
24512-63-8

geniposide

(1S,4aS,7S,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
265097-01-6

(1S,4aS,7S,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 37 percent / pyridine / 20 °C
2: 16.0 mg / pyridine
3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C
4: 23 percent / H2 / PtP2 / ethanol / 20 °C
View Scheme
geniposide
24512-63-8

geniposide

10-O-benzoyladoxoside tetraacetate

10-O-benzoyladoxoside tetraacetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 37 percent / pyridine / 20 °C
2: 16.0 mg / pyridine
3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C
4: 23 percent / H2 / PtP2 / ethanol / 20 °C
5: 100 percent / pyridine / 20 °C
View Scheme
geniposide
24512-63-8

geniposide

(1S,4aS,7aS)-7-Acetoxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

(1S,4aS,7aS)-7-Acetoxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 14 percent / pyridine / 20 °C
2: pyridine
View Scheme
geniposide
24512-63-8

geniposide

(1S,4aS,7aS)-1-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-trityloxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
265096-99-9

(1S,4aS,7aS)-1-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-trityloxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 37 percent / pyridine / 20 °C
2: 16.0 mg / pyridine
View Scheme
geniposide
24512-63-8

geniposide

6,7-dihydroapodantheroside
42830-26-2

6,7-dihydroapodantheroside

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h
2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C
View Scheme
geniposide
24512-63-8

geniposide

(4S,4aS,7S,7aR)-4-Hydroxy-7-hydroxymethyl-hexahydro-cyclopenta[c]pyran-3-one
256221-89-3

(4S,4aS,7S,7aR)-4-Hydroxy-7-hydroxymethyl-hexahydro-cyclopenta[c]pyran-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
View Scheme
geniposide
24512-63-8

geniposide

(S)-1-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopentyl)-ethane-1,2-diol
256221-90-6

(S)-1-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopentyl)-ethane-1,2-diol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
3: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h
2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C
3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C
3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C
View Scheme
geniposide
24512-63-8

geniposide

[(1R,2S,5S)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxymethyl-cyclopentyl]-methanol
256221-91-7

[(1R,2S,5S)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxymethyl-cyclopentyl]-methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
3: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C
4: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
View Scheme
Multi-step reaction with 3 steps
1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
3: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
View Scheme
Multi-step reaction with 4 steps
1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h
2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C
3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C
3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C
4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
View Scheme
geniposide
24512-63-8

geniposide

[(1S,2R,5S)-2-(6-Amino-purin-9-ylmethyl)-5-hydroxymethyl-cyclopentyl]-methanol

[(1S,2R,5S)-2-(6-Amino-purin-9-ylmethyl)-5-hydroxymethyl-cyclopentyl]-methanol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
3.1: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C
4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
5.1: NaH / tetrahydrofuran / 0 - 20 °C
5.2: Bu4NI / tetrahydrofuran / 20 °C
6.1: 1.86 g / aq. HCl / tetrahydrofuran / 24 h / 20 °C
7.1: H5IO6 / tetrahydrofuran / 0.25 h / 20 °C
7.2: K2CO3 / methanol / 4 h / 20 °C
7.3: 94 percent / NaBH4 / methanol / 16 h
8.1: 68.5 percent / Ph3P; DEAD / dioxane / 19 h / 20 °C
9.1: 97 percent / BCl3 / CH2Cl2 / -78 - -25 °C
View Scheme
Multi-step reaction with 9 steps
1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h
2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C
3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C
3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C
4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
5.1: NaH / tetrahydrofuran / 0 - 20 °C
5.2: Bu4NI / tetrahydrofuran / 20 °C
6.1: 1.86 g / aq. HCl / tetrahydrofuran / 24 h / 20 °C
7.1: H5IO6 / tetrahydrofuran / 0.25 h / 20 °C
7.2: K2CO3 / methanol / 4 h / 20 °C
7.3: 94 percent / NaBH4 / methanol / 16 h
8.1: 68.5 percent / Ph3P; DEAD / dioxane / 19 h / 20 °C
9.1: 97 percent / BCl3 / CH2Cl2 / -78 - -25 °C
View Scheme
geniposide
24512-63-8

geniposide

[(1S,2S,5S)-2-(6-Amino-purin-9-ylmethyl)-5-hydroxymethyl-cyclopentyl]-methanol

[(1S,2S,5S)-2-(6-Amino-purin-9-ylmethyl)-5-hydroxymethyl-cyclopentyl]-methanol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
3: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C
4: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
5: pyridine / CH2Cl2 / 4 - 20 °C
6: 1.47 g / aq. HCl / tetrahydrofuran / 34 h / 20 °C
7: H5IO6 / tetrahydrofuran / 0.5 h / 20 °C
8: 0.48 g / NaBH4 / CH2Cl2; ethanol / -78 - 20 °C
9: Ph3P; DEAD / tetrahydrofuran / 12 h / 20 °C
10: 35 percent / liq. NH3 / 72 h / 45 - 50 °C
View Scheme
Multi-step reaction with 10 steps
1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h
2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C
3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C
3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C
4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
5.1: pyridine / CH2Cl2 / 4 - 20 °C
6.1: 1.47 g / aq. HCl / tetrahydrofuran / 34 h / 20 °C
7.1: H5IO6 / tetrahydrofuran / 0.5 h / 20 °C
8.1: 0.48 g / NaBH4 / CH2Cl2; ethanol / -78 - 20 °C
9.1: Ph3P; DEAD / tetrahydrofuran / 12 h / 20 °C
10.1: 35 percent / liq. NH3 / 72 h / 45 - 50 °C
View Scheme

24512-63-8Relevant articles and documents

Guarnaccia et al.

, p. 5125 (1972)

Asymmetric total synthesis of the iridoid β-glucoside (+)-geniposide via phosphine organocatalysis

Jones, Regan A.,Krische, Michael J.

supporting information; experimental part, p. 1849 - 1851 (2009/09/06)

Phosphine-catalyzed [3 + 2] cycloaddition of ethyl-2, 3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the c/s-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.

The constituents of Eucommia ulmoides OLIV. IV. Isolation of a new sesquilignan glycoside and iridoids

Deyama,Ikawa,Kitagawa,Nishibe

, p. 4933 - 4938 (2007/10/02)

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