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32233-40-2

Basic Information
CAS No.: 32233-40-2
Name: (-)-Corey lactone diol
Molecular Structure:
Molecular Structure of 32233-40-2 ((-)-Corey lactone diol)
Formula: C8H12O4
Molecular Weight: 172.18
Synonyms: 2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-(hydroxymethyl)-, [3aR-(3aa,4a,5b,6aa)]-;2H-Cyclopenta[b]furan-2-one, hexahydro-5-hydroxy-4-(hydroxymethyl)-,stereoisomer (8CI);
EINECS: 608-721-8
Density: 1.365 g/cm3
Melting Point: 117-119 °C(lit.)
Boiling Point: 406.6 °C at 760 mmHg
Flash Point: 172.9 °C
Solubility:
Appearance: white to beige-brown cryst. powder or crystals
Hazard Symbols:
Risk Codes: R24/25
Safety: 24/25
Transport Information:
PSA: 66.76000
LogP: -0.70880
Synthetic route
58707-50-9, 72777-85-6, 81203-78-3, 65025-94-7

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In dichloromethane at 20℃; for 0.833333h; atmospheric pressure;99%
Multi-step reaction with 2 steps
1: 90 percent / PPTS / 1,2-dichloro-ethane / 2 h / Ambient temperature
2: 3,4-Dihydro-2H-pyran / TsOH
View Scheme
39746-00-4

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Stage #1: (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one With sodium methylate In methanol at 20℃; for 1.5h;
Stage #2: With hydrogenchloride In 1,4-dioxane; methanol at 20℃; pH=3 - 4;
97%
With sodium methylate In methanol at 20℃; for 2h;95%
117624-93-8

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate In methanol at 100℃; for 0.25h; Microwave irradiation;96%
With cerium (IV) sulfate tetrahydrate In methanol at 60℃; for 12h;96%
With aluminium(III) chloride hexahydrate In methanol at 100℃; for 0.25h; Solvent; Microwave irradiation; Sealed tube; chemoselective reaction;95%
26054-65-9

(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With Amberlite IR 120 resin In methanol at 70℃; for 8h;86%
31752-99-5

(-)-Corey lactone 5-(4-phenylbenzoate)

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With potassium carbonate In methanol; dichloromethane for 3h; Ambient temperature;85%
Multi-step reaction with 4 steps
1: 94 percent / imidazole / dimethylformamide / 1 h / Ambient temperature
2: 65 percent / CH3ONa / methanol / 1.33 h / Ambient temperature
3: 90 percent / PPTS / 1,2-dichloro-ethane / 2 h / Ambient temperature
4: 3,4-Dihydro-2H-pyran / TsOH
View Scheme

Biphenyl-4-carboxylic acid (3aR,4S,5R,6aS)-5-hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-ylmethyl ester

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; methanol for 4h; Ambient temperature;83%
62939-82-6

(3aR,4S,5R,6aS)-5-(acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With Amberlite IR 120 resin In methanol at 70℃; for 8h;82%
With hydrogenchloride In methanol; water for 4h; Reflux;82.1%
With DBN In methanol at 20℃; for 12h;
With methanol at 25 - 65℃;28 g
57930-46-8

(1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With Amberlite IR 120 resin In methanol at 70℃; for 8h;82%
With resin Wofatit SBW (OH-) In methanol for 2h; Ambient temperature;79%
50-00-0

formaldehyd

26054-46-6

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Stage #1: formaldehyd; (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one With formic acid; sulfuric acid at 80℃; for 24h;
Stage #2: With potassium carbonate In methanol at 0 - 20℃; for 2h;
79%
109122-52-3

(4aS,4bR,7aS,8aR)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

534-15-6

1,1-dimethoxyethane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 75 - 80℃; for 4h;A 78%
B n/a
159812-78-9

(E)-(4S,6R)-4,6-Dihydroxy-6-((S)-2-thioxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid methyl ester

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

159812-79-0

(3aR,4R,5R,6aS)-(-)-5-hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one

C

(2S,6S,8R,9R)-8-Hydroxy-5,11,12-trioxa-tricyclo[7.2.1.02,6]dodecan-4-one

D

((1R,2R,4S,5R)-2,4-Dihydroxy-7,9-dioxa-bicyclo[4.2.1]non-5-yl)-acetic acid methyl ester

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating; Further byproducts given;A 19%
B 44%
C 13%
D 8%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 19%
B 40%
C n/a
D n/a
159812-78-9

(E)-(4S,6R)-4,6-Dihydroxy-6-((S)-2-thioxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid methyl ester

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

159812-79-0

(3aR,4R,5R,6aS)-(-)-5-hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one

C

(2S,6S,8R,9R)-8-Hydroxy-5,11,12-trioxa-tricyclo[7.2.1.02,6]dodecan-4-one

D

(E)-(4S,6R,7S)-4,6,7,8-Tetrahydroxy-oct-2-enoic acid methyl ester

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating; Further byproducts given;A 19%
B 44%
C 13%
D 2%
159812-78-9

(E)-(4S,6R)-4,6-Dihydroxy-6-((S)-2-thioxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid methyl ester

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

159812-79-0

(3aR,4R,5R,6aS)-(-)-5-hydroxy-4-hydroxymethyl-hexahydro-cyclopenta[b]furan-2-one

C

(2S,6S,8R,9R)-8-Hydroxy-5,11,12-trioxa-tricyclo[7.2.1.02,6]dodecan-4-one

D

(S)-4-[(R)-1-Hydroxy-2-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-[1,3]oxathiolan-2-one

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating; Further byproducts given;A 19%
B 44%
C 13%
D 1%
90529-18-3

(1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

26054-65-9

(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one

C

76704-05-7

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

D

125226-81-5

(3aS,4R,5S,6aR)-5-acetoxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one

Conditions
ConditionsYield
With sodium hydroxide; Soerensen phosphate buffer In methanol at 36℃; for 24h; subtilisin DY; Further byproducts given. Yields of byproduct given;A n/a
B n/a
C 20%
D n/a
With sodium hydroxide; Soerensen phosphate buffer In methanol at 36℃; for 24h; subtilisin DY; Further byproducts given. Yields of byproduct given;A 16%
B n/a
C n/a
D n/a
110-87-2

3,4-dihydro-2H-pyran

65025-95-8

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

67788-45-8

(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one

Conditions
ConditionsYield
toluene-4-sulfonic acid Yields of byproduct given;A n/a
B 17%
65025-95-8

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

67788-45-8

(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one

Conditions
ConditionsYield
With 3,4-dihydro-2H-pyran; toluene-4-sulfonic acid Yield given;A n/a
B 17%
50-00-0

formaldehyd

26054-46-6

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

108-24-7

acetic anhydride

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

109122-52-3

(4aS,4bR,7aS,8aR)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid 1) 70 to 80 deg C, 20 h, sealed vessel, 2) 60 to 65 deg C, 40 h, sealed vessel, 3) RT, 20 h; Multistep reaction;
130325-32-5

Formic acid (3aR,4S,5R,6aS)-4-formyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With sodium methylate In methanol
With sodium In methanol at 0℃; for 0.5h;6.2 g
69222-61-3

(3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 25℃; Yield given;
90529-18-3

(1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

26054-65-9

(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one

C

76704-05-7

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

D

125226-81-5

(3aS,4R,5S,6aR)-5-acetoxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one

E

57930-46-8

(1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

F

125226-80-4

(1R,5S,6S,7S)-(+)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 36℃; for 24h; Product distribution; subtilisin DY, Soerensen phosphate buffer pH 7, further solvents, further enzymes;
51705-34-1, 39648-25-4

2-oxa-3-oxo-6-syn-hydroxymethyl-7-anti-acetoxy-cis-bicyclo[3,3,0]octane

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

76704-05-7

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

Conditions
ConditionsYield
With Wofatit SBW In methanol for 2h; Ambient temperature; Title compound not separated from byproducts;
134732-93-7

2-oxa-3-oxo-6-syn-acetoxymethyl-7-anti-hydroxy-cis-bicyclo[3,3,0]octane

A

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

B

76704-05-7

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

Conditions
ConditionsYield
With Wofatit SBW In methanol for 2h; Ambient temperature; Title compound not separated from byproducts;

(4aR,5S,7R,7aS)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-cyclopenta[c]pyran-3-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;
315716-34-8

(1S,2S,6R,8S)-10,10-dimethyl-5,9,11-trioxatricyclo[6.4.0.02,6]dodecan-4-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With Dowex 50wX8 In tetrahydrofuran; water at 20℃; for 3h;
7129-41-1

6-oxabicyclo[3.1.0]hex-2-ene

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 70 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C
2: 0.95 g / 30percent H2O2, 30 percent KOH / ethanol / 1.) 45 deg C, 1 h, 2.) reflux, 6 h
3: 91 percent / HCL / 0.67 h
4: 80 percent / pyridine / 1 h / 0 °C
5: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C
6: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h
7: 6.2 g / sodium / methanol / 0.5 h / 0 °C
View Scheme
26054-46-6

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h
2: 6.2 g / sodium / methanol / 0.5 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: H2SO4
2: MeONa / methanol
View Scheme
Multi-step reaction with 2 steps
1: 9.5 percent / glacial acetic acid, sulfuric acid / 24 h / 75 - 80 °C
2: 78 percent / p-toluenesulfonic acid / methanol / 4 h / 75 - 80 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / 24 h / 50 - 80 °C / Sealed tube
2: DBN / methanol / 12 h / 20 °C
View Scheme
49826-03-1

(-)-trans-2-carboxymethylcyclopent-3-en-1-ol

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 91 percent / HCL / 0.67 h
2: 80 percent / pyridine / 1 h / 0 °C
3: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C
4: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h
5: 6.2 g / sodium / methanol / 0.5 h / 0 °C
View Scheme
49826-01-9

methyl 2R-methylsulfonyloxy-4-cyclopentene-1R-acetate

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C
2: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h
3: 6.2 g / sodium / methanol / 0.5 h / 0 °C
View Scheme
49825-99-2

(-)-trans-2-methoxycarbonylmethylcyclopent-3-en-1-ol

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / pyridine / 1 h / 0 °C
2: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C
3: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h
4: 6.2 g / sodium / methanol / 0.5 h / 0 °C
View Scheme
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

76-83-5

trityl chloride

62939-85-9

(-)-7α-hydroxy-6β-triphenylmethoxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;100%
With pyridine In dichloromethane93%
With pyridine at 20℃; for 48h;87%
In pyridine at 20℃; for 48h; Substitution;87%
With pyridine at 20℃; for 12h; Temperature; Large scale;
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

13154-24-0

triisopropylsilyl chloride

1236109-24-2

[(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4(triisopropylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one]

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane for 15h;100%
Stage #1: (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one; triisopropylsilyl chloride With 1H-imidazole In dichloromethane for 15h;
Stage #2: With hydrogenchloride In dichloromethane; water at 0℃; pH=3 - 4;
100%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

18162-48-6

tert-butyldimethylsilyl chloride

117624-93-8

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 3h; Inert atmosphere;100%
With 1H-imidazole In dichloromethane at 0 - 40℃; for 24h; Inert atmosphere;95%
With 1H-imidazole; dmap In dichloromethane at 0 - 30℃; for 16h;340 g
With 1H-imidazole In dichloromethane at 40℃; Inert atmosphere;23 g
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

80522-42-5

triisopropylsilyl trifluoromethanesulfonate

1236109-24-2

[(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4(triisopropylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one]

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;100%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

994-30-9

triethylsilyl chloride

128948-09-4

(-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
With pyridine at 60℃; for 1h;97%
With pyridine at 65℃; for 4h;94.55%
With pyridine at 60℃; for 1h;93%
With pyridine at 60℃; for 1h;93%
With 1H-imidazole In N,N-dimethyl-formamide at 5℃; for 4h; Inert atmosphere;
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

18162-48-6

tert-butyldimethylsilyl chloride

58707-50-9, 72777-85-6, 81203-78-3, 65025-94-7

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 10℃; for 2h;96.3%
With 1H-imidazole In dichloromethane at 20℃;94.5%
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 1h;89%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

62961-72-2

Corey aldehyde

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -78℃; for 1.03333h; Reagent/catalyst; Solvent; Temperature;95%
With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -78℃; for 1h; Reagent/catalyst; Solvent; Temperature;95%
With oxalyl dichloride; triethylamine In dimethyl sulfoxide
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

14002-51-8

4-biphenyl-carboxylic acid chloride

31752-99-5

(-)-Corey lactone 5-(4-phenylbenzoate)

Conditions
ConditionsYield
Stage #1: (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one With pyridine; trityl chloride at 20℃; for 12h; Large scale;
Stage #2: 4-biphenyl-carboxylic acid chloride at 30℃; for 4.5h; Temperature; Large scale;
93.45%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

994-30-9

triethylsilyl chloride

C14H26O4Si

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 30℃; for 2h; Temperature; Solvent; Reagent/catalyst;92%
67-56-1

methanol

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

methyl (1R,2R,3R,5R)-(5-chloro-2-chloromethyl-3-hydroxycyclopentyl)acetate

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 7h;92%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

118457-23-1

7α-hydroxy-6β-hydroxymethylene-2-oxabicyclo<3.3.0>octan-3-one bistrimethylsilyl ether

Conditions
ConditionsYield
at 145℃; for 1h;90%
108-05-4

vinyl acetate

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

57930-46-8

(1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
With ALPS at 40℃; for 24h;90%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

69739-34-0

t-butyldimethylsiyl triflate

117624-93-8

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at -20 - 20℃; Inert atmosphere;89.4%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

2186-92-7

p-Anisaldehyde dimethyl acetal

1210039-33-0

C16H18O5

Conditions
ConditionsYield
4-methoxybenzoic acid In toluene at 120℃; for 3h; Dean-Stark apparatus;87%
110-87-2

3,4-dihydro-2H-pyran

32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

67788-45-8

(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one

Conditions
ConditionsYield
toluene-4-sulfonic acid In dichloromethane for 1.5h; Ambient temperature;84%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

58479-61-1

tert-butylchlorodiphenylsilane

84786-80-1

(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4-[(tert-butyldiphenylsilyloxy)methyl]-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at -40℃; for 2h;84%
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 2h;
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

18162-48-6

tert-butyldimethylsilyl chloride

39968-95-1

(3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 8h; Reagent/catalyst;83%
With 1H-imidazole In dichloromethane at 20℃; for 8h;82%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

98-88-4

benzoyl chloride

((3aS,4R,5S,6aR)-5-(benzoyloxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-yl)methyl benzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; enantioselective reaction;80%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

18162-48-6

tert-butyldimethylsilyl chloride

A

58707-50-9, 72777-85-6, 81203-78-3, 65025-94-7

(3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

B

117624-93-8

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane 1.) -20 deg C, 1.5 h, 2.) room temperature, 16 h;A 76%
B 4%
32233-40-2

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

98-59-9

p-toluenesulfonyl chloride

1063693-23-1

(3aR,4S,5R,6aS)-5-p-toluenesulfoxy-4-[(p-toluenesulfoxy)methyl]hexahydrocyclopenta[b]furan-2-one

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 3h;73%
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Chemistry

Molecular Structure of 2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-(hydroxymethyl)-, (3aR,4S,5R,6aS)- (CAS NO.32233-40-2):

IUPAC Name: (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one 
Empirical Formula: C8H12O4
Molecular Weight: 172.18
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 66.76 Å2
Index of Refraction: 1.545
Molar Refractivity: 39.88 cm3
Molar Volume: 126 cm3
Surface Tension: 54.6 dyne/cm
Density: 1.365 g/cm3
Flash Point: 176.7 °C
Enthalpy of Vaporization: 77.2 kJ/mol
Boiling Point: 415.2 °C at 760 mmHg
Vapour Pressure: 1.25E-08 mmHg at 25°C
Melting point: 117-119 °C(lit.)
Storage temp: -20°C
Product Categories: Prostaglandins; Latanoprost

Safety Profile

Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

Specification

  2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-(hydroxymethyl)-, (3aR,4S,5R,6aS)- , with CAS number of 32233-40-2, can be called Corey lactone diol;(3ar,4s,5r,6as)-(-)-hexahydro-5-hydroxy-4-(hydroxymethyl)-2h-cyclopent a[b]furan-2-one ; (3ar,4s,5r,6as)-hexahydro-5-hydroxy-4-(hydroxymethyl)-2h-cyclopenta[b]furan-2-one ; (-)-6beta-hydroxymethyl-7alpha-hydroxy-cis-2-oxabicyclo[3.3.0]octan-3-one ; (3ar,4s,5r,6as)-(-)-hexahydro-5-hydroxy- 4-hoch2-2h-cyclopenta(b)furan-2-one, 98%;hexahydro-5-hydroxy-4-(hydroxymethyl)-2h-cyclopenta[b]furan-2-one. ; (-)-corey diol (corey lactone) ; (-)-6beta-hydroxymethyl-7alpha-hydroxy-cis-2-oxabicyclo[3.3.0]octan-3-one .It is a white to beige-brown cryst. powder or crystal .

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