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743-51-1

743-51-1

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743-51-1 Usage

General Description

Bysochlamidacid is a naturally occurring chemical compound that is produced by certain types of fungi. It is known for its pharmacological properties, including antifungal and antibacterial activities. Bysochlamidacid has also shown potential in inhibiting certain enzymes and has been studied for its potential in drug discovery and development. Additionally, research has shown that Bysochlamidacid has significant potential as a lead compound for developing new drugs to combat diseases caused by different types of fungi and bacteria. Overall, Bysochlamidacid is a promising area of research for its potential medicinal applications.

Check Digit Verification of cas no

The CAS Registry Mumber 743-51-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,4 and 3 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 743-51:
(5*7)+(4*4)+(3*3)+(2*5)+(1*1)=71
71 % 10 = 1
So 743-51-1 is a valid CAS Registry Number.

743-51-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 10-ethyl-4-propyl-4,5,10,11-tetrahydro-1H-cyclonona[1,2-c:5,6-c']difuran-1,3,6,8(9H)-tetraone

1.2 Other means of identification

Product number -
Other names -

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:743-51-1 SDS

743-51-1Synthetic route

(1Z,5Z)-(R)-8-Ethyl-3-propyl-cyclonona-1,5-diene-1,2,5,6-tetracarboxylic acid

(1Z,5Z)-(R)-8-Ethyl-3-propyl-cyclonona-1,5-diene-1,2,5,6-tetracarboxylic acid

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
With hydrogenchloride dehydrative cyclization;
4-ethylcyclohexanone
5441-51-0

4-ethylcyclohexanone

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: 93 percent / NaH / benzene / 1.5 h / Heating
2.1: Br2 / diethyl ether / 2.17 h / 0 °C
3.1: 39 percent / methanol / 0 - 20 °C
4.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
5.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
6.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
7.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
7.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
8.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
9.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
10.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
11.1: aq. HF / acetonitrile / 1.5 h / 20 °C
12.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
13.1: CH2Cl2 / Photolysis
14.1: aq. LiOH / dioxane / 1.5 h / 50 °C
15.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
16.1: aq. HCl
View Scheme
Multi-step reaction with 16 steps
1.1: 93 percent / NaH / benzene / 1.5 h / Heating
2.1: Br2 / diethyl ether / 2.17 h / 0 °C
3.1: 39 percent / methanol / 0 - 20 °C
4.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
5.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
6.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
7.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
7.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
8.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
9.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
10.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
11.1: aq. HF / acetonitrile / 1.5 h / 20 °C
12.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
13.1: CH2Cl2 / Photolysis
13.2: toluene / Heating
14.1: aq. LiOH / dioxane / 1.5 h / 50 °C
15.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
16.1: aq. HCl
View Scheme
methyl 5-ethyl-2-oxo-cyclohexancarboxylate
114862-60-1

methyl 5-ethyl-2-oxo-cyclohexancarboxylate

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: Br2 / diethyl ether / 2.17 h / 0 °C
2.1: 39 percent / methanol / 0 - 20 °C
3.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
5.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
6.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
6.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
7.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
8.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
9.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
10.1: aq. HF / acetonitrile / 1.5 h / 20 °C
11.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
12.1: CH2Cl2 / Photolysis
13.1: aq. LiOH / dioxane / 1.5 h / 50 °C
14.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
15.1: aq. HCl
View Scheme
Multi-step reaction with 15 steps
1.1: Br2 / diethyl ether / 2.17 h / 0 °C
2.1: 39 percent / methanol / 0 - 20 °C
3.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
5.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
6.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
6.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
7.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
8.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
9.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
10.1: aq. HF / acetonitrile / 1.5 h / 20 °C
11.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
12.1: CH2Cl2 / Photolysis
12.2: toluene / Heating
13.1: aq. LiOH / dioxane / 1.5 h / 50 °C
14.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
15.1: aq. HCl
View Scheme
3-n-propylcyclobut-1-en-1,2-dicarboxylic acid
144226-91-5

3-n-propylcyclobut-1-en-1,2-dicarboxylic acid

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
2: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
3: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
4: aq. HF / acetonitrile / 1.5 h / 20 °C
5: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
6: CH2Cl2 / Photolysis
7: aq. LiOH / dioxane / 1.5 h / 50 °C
8: KMnO4 / H2O; dioxane / 1 h / 40 °C
9: aq. HCl
View Scheme
Multi-step reaction with 9 steps
1.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
2.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
3.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
4.1: aq. HF / acetonitrile / 1.5 h / 20 °C
5.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
6.1: CH2Cl2 / Photolysis
6.2: toluene / Heating
7.1: aq. LiOH / dioxane / 1.5 h / 50 °C
8.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
9.1: aq. HCl
View Scheme
dimethyl 4-ethylcyclopenten-1,2-dicarboxylate
144226-93-7

dimethyl 4-ethylcyclopenten-1,2-dicarboxylate

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
2.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
2.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
3.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
4.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
4.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
5.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
6.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
7.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
8.1: aq. HF / acetonitrile / 1.5 h / 20 °C
9.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
10.1: CH2Cl2 / Photolysis
11.1: aq. LiOH / dioxane / 1.5 h / 50 °C
12.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
13.1: aq. HCl
View Scheme
Multi-step reaction with 13 steps
1.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
2.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
2.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
3.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
4.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
4.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
5.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
6.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
7.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
8.1: aq. HF / acetonitrile / 1.5 h / 20 °C
9.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
10.1: CH2Cl2 / Photolysis
10.2: toluene / Heating
11.1: aq. LiOH / dioxane / 1.5 h / 50 °C
12.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
13.1: aq. HCl
View Scheme
dimethyl 3-n-propylcyclobut-1-en-1,2-dicarboxylate
144226-90-4

dimethyl 3-n-propylcyclobut-1-en-1,2-dicarboxylate

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
2: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
3: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
4: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
5: aq. HF / acetonitrile / 1.5 h / 20 °C
6: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
7: CH2Cl2 / Photolysis
8: aq. LiOH / dioxane / 1.5 h / 50 °C
9: KMnO4 / H2O; dioxane / 1 h / 40 °C
10: aq. HCl
View Scheme
Multi-step reaction with 10 steps
1.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
2.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
3.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
5.1: aq. HF / acetonitrile / 1.5 h / 20 °C
6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
7.1: CH2Cl2 / Photolysis
7.2: toluene / Heating
8.1: aq. LiOH / dioxane / 1.5 h / 50 °C
9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
10.1: aq. HCl
View Scheme
1,3-Dibromo-5-ethyl-2-oxo-cyclohexanecarboxylic acid methyl ester
144226-92-6

1,3-Dibromo-5-ethyl-2-oxo-cyclohexanecarboxylic acid methyl ester

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: 39 percent / methanol / 0 - 20 °C
2.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
4.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
5.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
5.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
6.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
7.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
8.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
9.1: aq. HF / acetonitrile / 1.5 h / 20 °C
10.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
11.1: CH2Cl2 / Photolysis
12.1: aq. LiOH / dioxane / 1.5 h / 50 °C
13.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
14.1: aq. HCl
View Scheme
Multi-step reaction with 14 steps
1.1: 39 percent / methanol / 0 - 20 °C
2.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
4.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
5.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
5.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
6.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
7.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
8.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
9.1: aq. HF / acetonitrile / 1.5 h / 20 °C
10.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
11.1: CH2Cl2 / Photolysis
11.2: toluene / Heating
12.1: aq. LiOH / dioxane / 1.5 h / 50 °C
13.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
14.1: aq. HCl
View Scheme
1-Bromo-4-propyl-cyclobutane-1,2-dicarboxylic acid

1-Bromo-4-propyl-cyclobutane-1,2-dicarboxylic acid

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: diethyl ether / 1 h / 0 °C
2: 5.60 g / DBU / CHCl3 / 1 h / Heating
3: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
4: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
5: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
6: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
7: aq. HF / acetonitrile / 1.5 h / 20 °C
8: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
9: CH2Cl2 / Photolysis
10: aq. LiOH / dioxane / 1.5 h / 50 °C
11: KMnO4 / H2O; dioxane / 1 h / 40 °C
12: aq. HCl
View Scheme
Multi-step reaction with 12 steps
1.1: diethyl ether / 1 h / 0 °C
2.1: 5.60 g / DBU / CHCl3 / 1 h / Heating
3.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
4.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
5.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
7.1: aq. HF / acetonitrile / 1.5 h / 20 °C
8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
9.1: CH2Cl2 / Photolysis
9.2: toluene / Heating
10.1: aq. LiOH / dioxane / 1.5 h / 50 °C
11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
12.1: aq. HCl
View Scheme
1-Bromo-4-propyl-cyclobutane-1,2-dicarboxylic acid dimethyl ester

1-Bromo-4-propyl-cyclobutane-1,2-dicarboxylic acid dimethyl ester

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 5.60 g / DBU / CHCl3 / 1 h / Heating
2: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
3: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
4: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
5: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
6: aq. HF / acetonitrile / 1.5 h / 20 °C
7: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
8: CH2Cl2 / Photolysis
9: aq. LiOH / dioxane / 1.5 h / 50 °C
10: KMnO4 / H2O; dioxane / 1 h / 40 °C
11: aq. HCl
View Scheme
Multi-step reaction with 11 steps
1.1: 5.60 g / DBU / CHCl3 / 1 h / Heating
2.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
3.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
4.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
6.1: aq. HF / acetonitrile / 1.5 h / 20 °C
7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
8.1: CH2Cl2 / Photolysis
8.2: toluene / Heating
9.1: aq. LiOH / dioxane / 1.5 h / 50 °C
10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
11.1: aq. HCl
View Scheme
methyl (4R)-4-ethyl-2-hydroxymethylcyclopent-1-encarboxylate
301670-57-5

methyl (4R)-4-ethyl-2-hydroxymethylcyclopent-1-encarboxylate

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
2.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
2.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
3.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
4.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
6.1: aq. HF / acetonitrile / 1.5 h / 20 °C
7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
8.1: CH2Cl2 / Photolysis
9.1: aq. LiOH / dioxane / 1.5 h / 50 °C
10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
11.1: aq. HCl
View Scheme
Multi-step reaction with 11 steps
1.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
2.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
2.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
3.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
4.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
6.1: aq. HF / acetonitrile / 1.5 h / 20 °C
7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
8.1: CH2Cl2 / Photolysis
8.2: toluene / Heating
9.1: aq. LiOH / dioxane / 1.5 h / 50 °C
10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
11.1: aq. HCl
View Scheme
(R)-4-Ethyl-cyclopent-1-ene-1,2-dicarboxylic acid monomethyl ester
301670-38-2

(R)-4-Ethyl-cyclopent-1-ene-1,2-dicarboxylic acid monomethyl ester

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
1.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
2.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
3.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
3.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
4.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
5.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
7.1: aq. HF / acetonitrile / 1.5 h / 20 °C
8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
9.1: CH2Cl2 / Photolysis
10.1: aq. LiOH / dioxane / 1.5 h / 50 °C
11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
12.1: aq. HCl
View Scheme
Multi-step reaction with 12 steps
1.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
1.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
2.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
3.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
3.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
4.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
5.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
7.1: aq. HF / acetonitrile / 1.5 h / 20 °C
8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
9.1: CH2Cl2 / Photolysis
9.2: toluene / Heating
10.1: aq. LiOH / dioxane / 1.5 h / 50 °C
11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
12.1: aq. HCl
View Scheme
3-propyl-cyclobut-1-ene-1,2-dicarboxylic acid 2-methylsulfanylmethyl ester
301670-67-7

3-propyl-cyclobut-1-ene-1,2-dicarboxylic acid 2-methylsulfanylmethyl ester

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
2: aq. HF / acetonitrile / 1.5 h / 20 °C
3: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
4: CH2Cl2 / Photolysis
5: aq. LiOH / dioxane / 1.5 h / 50 °C
6: KMnO4 / H2O; dioxane / 1 h / 40 °C
7: aq. HCl
View Scheme
Multi-step reaction with 7 steps
1.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
2.1: aq. HF / acetonitrile / 1.5 h / 20 °C
3.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
4.1: CH2Cl2 / Photolysis
4.2: toluene / Heating
5.1: aq. LiOH / dioxane / 1.5 h / 50 °C
6.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
7.1: aq. HCl
View Scheme
bis-(methylthio)methyl 3-n-propylcyclobut-1-en-1,2-dicarboxylate
301670-65-5

bis-(methylthio)methyl 3-n-propylcyclobut-1-en-1,2-dicarboxylate

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
2: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
3: aq. HF / acetonitrile / 1.5 h / 20 °C
4: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
5: CH2Cl2 / Photolysis
6: aq. LiOH / dioxane / 1.5 h / 50 °C
7: KMnO4 / H2O; dioxane / 1 h / 40 °C
8: aq. HCl
View Scheme
Multi-step reaction with 8 steps
1.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
2.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
3.1: aq. HF / acetonitrile / 1.5 h / 20 °C
4.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
5.1: CH2Cl2 / Photolysis
5.2: toluene / Heating
6.1: aq. LiOH / dioxane / 1.5 h / 50 °C
7.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
8.1: aq. HCl
View Scheme
(4R)-4-ethyl-2-(tert-butyldimethylsilyloxy)methylcyclopent-1-enmethanol
301670-62-2

(4R)-4-ethyl-2-(tert-butyldimethylsilyloxy)methylcyclopent-1-enmethanol

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
2: aq. HF / acetonitrile / 1.5 h / 20 °C
3: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
4: CH2Cl2 / Photolysis
5: aq. LiOH / dioxane / 1.5 h / 50 °C
6: KMnO4 / H2O; dioxane / 1 h / 40 °C
7: aq. HCl
View Scheme
Multi-step reaction with 7 steps
1.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
2.1: aq. HF / acetonitrile / 1.5 h / 20 °C
3.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
4.1: CH2Cl2 / Photolysis
4.2: toluene / Heating
5.1: aq. LiOH / dioxane / 1.5 h / 50 °C
6.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
7.1: aq. HCl
View Scheme
(4S)-4-ethyl-2-(2-tetrahydropyranyloxy)methylcyclopent-1-enmethanol
301670-59-7

(4S)-4-ethyl-2-(2-tetrahydropyranyloxy)methylcyclopent-1-enmethanol

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
2: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
3: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
4: aq. HF / acetonitrile / 1.5 h / 20 °C
5: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
6: CH2Cl2 / Photolysis
7: aq. LiOH / dioxane / 1.5 h / 50 °C
8: KMnO4 / H2O; dioxane / 1 h / 40 °C
9: aq. HCl
View Scheme
Multi-step reaction with 9 steps
1.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
2.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
3.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
4.1: aq. HF / acetonitrile / 1.5 h / 20 °C
5.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
6.1: CH2Cl2 / Photolysis
6.2: toluene / Heating
7.1: aq. LiOH / dioxane / 1.5 h / 50 °C
8.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
9.1: aq. HCl
View Scheme
methyl (4R)-4-ethyl-2-(2-tetrahydropyranyloxy)methylcyclopent-1-encarboxylate
301670-58-6

methyl (4R)-4-ethyl-2-(2-tetrahydropyranyloxy)methylcyclopent-1-encarboxylate

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
1.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
3.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
5.1: aq. HF / acetonitrile / 1.5 h / 20 °C
6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
7.1: CH2Cl2 / Photolysis
8.1: aq. LiOH / dioxane / 1.5 h / 50 °C
9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
10.1: aq. HCl
View Scheme
Multi-step reaction with 10 steps
1.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
1.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
3.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
5.1: aq. HF / acetonitrile / 1.5 h / 20 °C
6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
7.1: CH2Cl2 / Photolysis
7.2: toluene / Heating
8.1: aq. LiOH / dioxane / 1.5 h / 50 °C
9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
10.1: aq. HCl
View Scheme
(R)-14-Ethyl-6-propyl-3,10-dioxa-tricyclo[10.3.0.05,8]pentadeca-1(12),5(8)-diene-4,9-dione
302350-30-7

(R)-14-Ethyl-6-propyl-3,10-dioxa-tricyclo[10.3.0.05,8]pentadeca-1(12),5(8)-diene-4,9-dione

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: CH2Cl2 / Photolysis
2: aq. LiOH / dioxane / 1.5 h / 50 °C
3: KMnO4 / H2O; dioxane / 1 h / 40 °C
4: aq. HCl
View Scheme
Multi-step reaction with 4 steps
1.1: CH2Cl2 / Photolysis
1.2: toluene / Heating
2.1: aq. LiOH / dioxane / 1.5 h / 50 °C
3.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
4.1: aq. HCl
View Scheme
10-ethyl-4-propyl-4,5,8,9,10,11-hexahydro-1H-2,7-dioxa-dicyclopenta[a,e]cyclononene-3,6-dione
302350-31-8

10-ethyl-4-propyl-4,5,8,9,10,11-hexahydro-1H-2,7-dioxa-dicyclopenta[a,e]cyclononene-3,6-dione

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. LiOH / dioxane / 1.5 h / 50 °C
2: KMnO4 / H2O; dioxane / 1 h / 40 °C
3: aq. HCl
View Scheme
(4R)-1-(tert-butyldimethylsilyloxy)methyl-4-ethyl-2-(2-tetrahydropyranyloxy)methyl-cyclopent-1-ene
301670-60-0

(4R)-1-(tert-butyldimethylsilyloxy)methyl-4-ethyl-2-(2-tetrahydropyranyloxy)methyl-cyclopent-1-ene

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
2: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
3: aq. HF / acetonitrile / 1.5 h / 20 °C
4: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
5: CH2Cl2 / Photolysis
6: aq. LiOH / dioxane / 1.5 h / 50 °C
7: KMnO4 / H2O; dioxane / 1 h / 40 °C
8: aq. HCl
View Scheme
Multi-step reaction with 8 steps
1.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
2.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
3.1: aq. HF / acetonitrile / 1.5 h / 20 °C
4.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
5.1: CH2Cl2 / Photolysis
5.2: toluene / Heating
6.1: aq. LiOH / dioxane / 1.5 h / 50 °C
7.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
8.1: aq. HCl
View Scheme
3-Propyl-cyclobut-1-ene-1,2-dicarboxylic acid 1-((S)-4-ethyl-2-hydroxymethyl-cyclopent-1-enylmethyl) ester 2-methylsulfanylmethyl ester

3-Propyl-cyclobut-1-ene-1,2-dicarboxylic acid 1-((S)-4-ethyl-2-hydroxymethyl-cyclopent-1-enylmethyl) ester 2-methylsulfanylmethyl ester

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
2: CH2Cl2 / Photolysis
3: aq. LiOH / dioxane / 1.5 h / 50 °C
4: KMnO4 / H2O; dioxane / 1 h / 40 °C
5: aq. HCl
View Scheme
Multi-step reaction with 5 steps
1.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
2.1: CH2Cl2 / Photolysis
2.2: toluene / Heating
3.1: aq. LiOH / dioxane / 1.5 h / 50 °C
4.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
5.1: aq. HCl
View Scheme
(1Z,4Z)-(R)-7-Ethyl-5,9-bis-hydroxymethyl-2-propyl-cyclonona-4,9-diene-1,4-dicarboxylic acid

(1Z,4Z)-(R)-7-Ethyl-5,9-bis-hydroxymethyl-2-propyl-cyclonona-4,9-diene-1,4-dicarboxylic acid

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KMnO4 / H2O; dioxane / 1 h / 40 °C
2: aq. HCl
View Scheme
3-propyl-cyclobut-1-ene-1,2-dicarboxylic acid 1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethyl-cyclopent-1-enylmethyl] ester 2-methylsulfanylmethyl ester
301670-69-9

3-propyl-cyclobut-1-ene-1,2-dicarboxylic acid 1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethyl-cyclopent-1-enylmethyl] ester 2-methylsulfanylmethyl ester

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: aq. HF / acetonitrile / 1.5 h / 20 °C
2: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
3: CH2Cl2 / Photolysis
4: aq. LiOH / dioxane / 1.5 h / 50 °C
5: KMnO4 / H2O; dioxane / 1 h / 40 °C
6: aq. HCl
View Scheme
Multi-step reaction with 6 steps
1.1: aq. HF / acetonitrile / 1.5 h / 20 °C
2.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
3.1: CH2Cl2 / Photolysis
3.2: toluene / Heating
4.1: aq. LiOH / dioxane / 1.5 h / 50 °C
5.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
6.1: aq. HCl
View Scheme
C10H10O5

C10H10O5

(+)-byssochlamic acid
743-51-1

(+)-byssochlamic acid

Conditions
ConditionsYield
With BfL10 ketosteroid isomerase obtained from E. coli Reagent/catalyst; Enzymatic reaction;

743-51-1Downstream Products

743-51-1Relevant articles and documents

In vitro studies of maleidride-forming enzymes

Yin, Sen,Friedrich, Steffen,Hrupins, Vjaceslavs,Cox, Russell J.

, p. 14922 - 14931 (2021/05/19)

In vitro assays of enzymes involved in the biosynthesis of maleidrides from polyketides in fungi were performed. The results show that the enzymes are closely related to primary metabolism enzymes of the citric acid cycle in terms of stereochemical preferences, but with an expanded substrate selectivity. A key citrate synthase can react both saturated and unsaturated acyl CoA substrates to give solely anti substituted citrates. This undergoes anti-dehydration to afford an unsaturated precursor which is cyclised in vitro by ketosteroid-isomerase-like enzymes to give byssochlamic acid. This journal is

Total Synthesis of (+/-)-Byssochlamic Acid

White, James D.,Dillon, Michael P.,Butlin, Roger J.

, p. 9673 - 9674 (2007/10/02)

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