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57103-57-8

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Basic Information
CAS No.: 57103-57-8
Name: glyceollin
Article Data: 4
Molecular Structure:
Molecular Structure of 57103-57-8 (glyceollin)
Formula: C20H18 O5
Molecular Weight: 338.36
Synonyms: 2H,6H-Benzofuro[3,2-c]pyrano[2,3-h][1]benzopyran-6a,9(11aH)-diol,2,2-dimethyl-, (6aS-cis)-; (-)-Glyceollin I; Glyceollin I
Density: 1.397g/cm3
Boiling Point: 527.4°Cat760mmHg
Flash Point: 272.7°C
PSA: 68.15000
LogP: 3.29010
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Synthetic route
1072145-68-6

(-)-9-(t-butyldimethylsilyloxy) glyceollin I

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
With triethylamine tris(hydrogen fluoride) In pyridine; dichloromethane at 20℃; for 6h; Inert atmosphere;90%
With triethylamine tris(hydrogen fluoride) In acetonitrile at -20 - 4℃; Inert atmosphere;77%
412339-25-4

4-benzyloxy-salicylalcohol

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium carbonate / acetone / Reflux; Inert atmosphere
2.1: acetonitrile / Inert atmosphere
3.1: potassium tert-butylate / methanol / Inert atmosphere; Reflux
4.1: triphenylphosphine hydrobromide / dichloromethane / 20 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether / dichloromethane / -20 °C
6.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 0 - 20 °C / 1810.07 Torr
7.1: 3-Methylpyridine / para-xylene / 18 h / 120 °C / Inert atmosphere
8.1: triethylamine tris(hydrogen fluoride) / pyridine; dichloromethane / 6 h / 20 °C / Inert atmosphere
View Scheme
1026107-41-4

2-benzyloxy-4-methoxymethylenoxyacetophenone

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: iodine; Selectfluor / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere
2.1: potassium carbonate / acetone / Reflux; Inert atmosphere
3.1: acetonitrile / Inert atmosphere
4.1: potassium tert-butylate / methanol / Inert atmosphere; Reflux
5.1: triphenylphosphine hydrobromide / dichloromethane / 20 °C / Inert atmosphere
5.2: 20 °C / Inert atmosphere
6.1: osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether / dichloromethane / -20 °C
7.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 0 - 20 °C / 1810.07 Torr
8.1: 3-Methylpyridine / para-xylene / 18 h / 120 °C / Inert atmosphere
9.1: triethylamine tris(hydrogen fluoride) / pyridine; dichloromethane / 6 h / 20 °C / Inert atmosphere
View Scheme
1072145-52-8

2-(5'-benzyloxy-2'-hydroxymethyl)phenoxy-1-(2'-benzyloxy-4'-methoxy-methylenoxy)phenylethanone

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: acetonitrile / Inert atmosphere
2.1: potassium tert-butylate / methanol / Inert atmosphere; Reflux
3.1: triphenylphosphine hydrobromide / dichloromethane / 20 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether / dichloromethane / -20 °C
5.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 0 - 20 °C / 1810.07 Torr
6.1: 3-Methylpyridine / para-xylene / 18 h / 120 °C / Inert atmosphere
7.1: triethylamine tris(hydrogen fluoride) / pyridine; dichloromethane / 6 h / 20 °C / Inert atmosphere
View Scheme

Br(1-)*C49H44O6P(1+)

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium tert-butylate / methanol / Inert atmosphere; Reflux
2.1: triphenylphosphine hydrobromide / dichloromethane / 20 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether / dichloromethane / -20 °C
4.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 0 - 20 °C / 1810.07 Torr
5.1: 3-Methylpyridine / para-xylene / 18 h / 120 °C / Inert atmosphere
6.1: triethylamine tris(hydrogen fluoride) / pyridine; dichloromethane / 6 h / 20 °C / Inert atmosphere
View Scheme
1072145-53-9

2',7-(dibenzyloxy)-4'-(methoxymethyloxy)isoflav-3-ene

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triphenylphosphine hydrobromide / dichloromethane / 20 °C / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether / dichloromethane / -20 °C
3.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 0 - 20 °C / 1810.07 Torr
4.1: 3-Methylpyridine / para-xylene / 18 h / 120 °C / Inert atmosphere
5.1: triethylamine tris(hydrogen fluoride) / pyridine; dichloromethane / 6 h / 20 °C / Inert atmosphere
View Scheme
1072145-54-0

2',7-dibenzyloxy-4'-(tert-butyldimethylsilyloxy)isoflav-3-ene

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether / dichloromethane / -20 °C
2: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 0 - 20 °C / 1810.07 Torr
3: 3-Methylpyridine / para-xylene / 18 h / 120 °C / Inert atmosphere
4: triethylamine tris(hydrogen fluoride) / pyridine; dichloromethane / 6 h / 20 °C / Inert atmosphere
View Scheme
1072145-55-1

(+)-4'-tert-butyldimethylsilyloxy-2',7-(dibenzyloxy)isoflavan-3,4-diol

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 0 - 20 °C / 1810.07 Torr
2: 3-Methylpyridine / para-xylene / 18 h / 120 °C / Inert atmosphere
3: triethylamine tris(hydrogen fluoride) / pyridine; dichloromethane / 6 h / 20 °C / Inert atmosphere
View Scheme
1740-74-5

1,1-diethoxy-3-methyl-2-butene

1072145-64-2

(-)-9-(tert-butyldimethylsilyloxy)glycinol

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3-Methylpyridine / para-xylene / 18 h / 120 °C / Inert atmosphere
2: triethylamine tris(hydrogen fluoride) / pyridine; dichloromethane / 6 h / 20 °C / Inert atmosphere
View Scheme
1072145-51-7

1-(2'-benzyloxy-4'-methoxymethylenoxy)phenyl-2-iodoethanone

57103-57-8

(+)-Glyceollin I

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium carbonate / acetone / Reflux; Inert atmosphere
2.1: acetonitrile / Inert atmosphere
3.1: potassium tert-butylate / methanol / Inert atmosphere; Reflux
4.1: triphenylphosphine hydrobromide / dichloromethane / 20 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: osmium(VIII) oxide; hydroquinidine 1 4-phthalazinediyl diether / dichloromethane / -20 °C
6.1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 0 - 20 °C / 1810.07 Torr
7.1: 3-Methylpyridine / para-xylene / 18 h / 120 °C / Inert atmosphere
8.1: triethylamine tris(hydrogen fluoride) / pyridine; dichloromethane / 6 h / 20 °C / Inert atmosphere
View Scheme
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