• Name

  L-QUEBRACHITOL

• EINECS
• CAS No. 642-38-6
• Article Data15
• CAS DataBase
• Density 1.56 g/cm³
• Solubility Soluble
• Melting Point 189 - 192 C
• Formula C7H14 O6
• Boiling Point 317.2 °C at 760 mmHg
• Molecular Weight 194.185
• Flash Point 145.6 °C
• Transport Information
• Appearance white to off-white crystals
• Safety 24/25-36-26
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Not regulated
• Synonyms Inositol,2-O-methyl- (6CI,7CI); Inositol, 2-O-methyl-, L-chiro- (8CI); (-)-Quebrachitol;2-O-Methyl-L-chiro-inositol; Brahol; L-(-)-2-O-Methylinositol; L-Quebrachitol;NSC 26254; Quebrachit; Quebrachitol; Quebrachitol, (-)-
• PSA 110.38000
• LogP -3.18050

Synthetic route

116-11-0

2-Methoxypropene

642-38-6

quebrachitol

58769-23-6

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol

Conditions

Conditions	Yield
With hydrogenchloride In N,N-dimethyl-formamide at 60℃; for 2h;	96%
camphor-10-sulfonic acid In N,N-dimethyl-formamide at 20 - 60℃; for 5h; Cyclization;	91%
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 60℃; for 4h;	85%

642-38-6

quebrachitol

38876-99-2

1L-chiro-inositol

Conditions

Conditions	Yield
With hydrogen iodide	93%
With hydrogen iodide for 2h; Heating;	80%
With hydrogen iodide

642-38-6

quebrachitol

98-88-4

benzoyl chloride

73803-06-2

L-1,3,4,5,6-penta-O-benzoyl-2-O-methyl-chiro-inositol

Conditions

Conditions	Yield
With pyridine at 80 - 90℃; for 6h;	89%
With dmap In pyridine at 20℃; Acylation;

642-38-6

quebrachitol

77-76-9

2,2-dimethoxy-propane

A

58769-23-6

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol

B

17230-37-4

1L-5,6-O-Isopropyliden-2-O-methyl-chiro-inosit

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80℃; for 20h;	A 85% B 10%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 16h; Ambient temperature;	A 6.9 g B n/a

...Expand

933-40-4

cycloxexanone dimethyl ketal

642-38-6

quebrachitol

A

6848-53-9

L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol

B

754197-57-4

1L-1,2-O-cyclohexylidene-5-O-methyl-chiro-inositol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20 - 105℃; for 22.5h;	A 71% B 9%

...Expand

642-38-6

quebrachitol

100-39-0

benzyl bromide

C42H44O6

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	55%

642-38-6

quebrachitol

125290-99-5

(1S,2S,3R,4S,5S,6S)-1-fluoro-2-O-(methyl)cyclohexane-2,3,4,5,6-pentol

Conditions

Conditions	Yield
With 4,4'-diaminostilbene-2,2'-disulfonic acid In dichloromethane at -30 - 20℃;	54%
With (diethylamido)sulfur trifluoride In dichloromethane 1.) -40 dec C to -30 deg C, 30 min, 2.) -20 deg C, 2.5 h, 3.) 0 deg C, 2.8 h then r.t., 30 min;	53%
With diethylamino-sulfur trifluoride In dichloromethane at 20℃; for 4h;

642-38-6

quebrachitol

98-88-4

benzoyl chloride

A

C21H22O8

B

C21H22O8

C

341524-05-8

C28H26O9

Conditions

Conditions	Yield
With pyridine at 0 - 10℃; for 6h;	A 20% B 20% C 50%

...Expand

642-38-6

quebrachitol

98-88-4

benzoyl chloride

A

73803-06-2

L-1,3,4,5,6-penta-O-benzoyl-2-O-methyl-chiro-inositol

B

341524-05-8

C28H26O9

C

341524-06-9

C35H30O10

Conditions

Conditions	Yield
With pyridine at 0 - 10℃; for 6h;	A 20% B 20% C 40%

...Expand

642-38-6

quebrachitol

3-deoxy-3-[18F]fluoro-O-methyl-myo-inositol

Conditions

Conditions	Yield
With 18F-fluoride; diethylamino-sulfur trifluoride In chloroform for 0.5h; Ambient temperature;	10.6%

642-38-6

quebrachitol

28079-67-6, 134356-41-5

(1S)-1,3,4,5,6-penta-O-nitro-2-O-methyl-asymm.-inositol

Conditions

Conditions	Yield
With sulfuric acid; nitric acid

642-38-6

quebrachitol

18685-70-6

chiro-inositol

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid at 160℃; Kochen des Reaktionsprodukts mit Wasser und Ba(OH)2;

75-77-4

chloro-trimethyl-silane

642-38-6

quebrachitol

14199-75-8, 14199-76-9, 14313-39-4, 14486-18-1, 75658-14-9, 92419-60-8, 92620-07-0, 92620-08-1, 92620-09-2, 92620-10-5, 92620-11-6

(2S,3R,5R,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane In pyridine

1122-84-5

1-ethoxycyclohexene

642-38-6

quebrachitol

6848-53-9

L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide

642-38-6

quebrachitol

A

125290-98-4

D-3-deoxy-3-fluoro-1-O-methyl-myo-inositol

B

125290-99-5

(1S,2S,3R,4S,5S,6S)-1-fluoro-2-O-(methyl)cyclohexane-2,3,4,5,6-pentol

Conditions

Conditions	Yield
With diethylamino-sulfur trifluoride at 20℃; for 0.75h; Yield given;

642-38-6

quebrachitol

77-76-9

2,2-dimethoxy-propane

58769-23-6

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol

642-38-6

quebrachitol

108-94-1

cyclohexanone

6848-53-9

L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene
With sulfuric acid In N,N-dimethyl-formamide; benzene

642-38-6

quebrachitol

484-68-4, 484-69-5, 523-92-2, 642-38-6, 3559-00-0, 3564-07-6, 6090-97-7, 7586-49-4, 7600-53-5, 10284-63-6, 17405-65-1, 22350-68-1, 23887-12-9, 32934-27-3, 35688-46-1, 56782-15-1, 58769-21-4, 60537-25-9, 64314-40-5, 74560-60-4, 103773-59-7, 111059-09-7, 115888-70-5, 144902-49-8, 484-71-9

bornesitol

Conditions

Conditions	Yield
With sulfuric acid; acetic acid Heating; Irradiation;

642-38-6

quebrachitol

3559-01-1, 5834-35-5, 20095-97-0, 92541-30-5, 92541-35-0, 92541-36-1

3-O-Methyl-D-myo-inosose-(1)

Conditions

Conditions	Yield
With oxygen; platinum on activated charcoal In water

7647-01-0

hydrogenchloride

642-38-6

quebrachitol

64-19-7

acetic acid

18685-70-6

chiro-inositol

Conditions

Conditions	Yield
at 160℃; Kochen des Reaktionsprodukts mit Ba(OH)2 in Wasser;

...Expand

642-38-6

quebrachitol

1L-1,2-di-O-methyl-chiro-inositol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / p-TsOH*H2O / dimethylformamide / 22.5 h / 20 - 105 °C 2: 94 percent / NaH / dimethylformamide / 0 - 20 °C 3: 71 percent / aq. HCl / methanol / 20 °C View Scheme

642-38-6

quebrachitol

904689-58-3

1L-3,4:5,6-di-O-cyclohexylidene-1,2-di-O-methyl-chiro-inositol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / p-TsOH*H2O / dimethylformamide / 22.5 h / 20 - 105 °C 2: 94 percent / NaH / dimethylformamide / 0 - 20 °C View Scheme

642-38-6

quebrachitol

60504-85-0, 128442-40-0, 131432-85-4, 131432-88-7

1L-1-O-benzoyl-3,4:5,6-di-O-cyclohexylidene-2-O-methyl-chiro-inositol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / p-TsOH*H2O / dimethylformamide / 22.5 h / 20 - 105 °C 2: 98 percent / DMAP; Et3N / CH2Cl2 / 120 h / 20 °C View Scheme

642-38-6

quebrachitol

725273-54-1

1-O-benzoyl-2-O-methyl-(-)-chiro-inositol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / p-TsOH*H2O / dimethylformamide / 22.5 h / 20 - 105 °C 2: 98 percent / DMAP; Et3N / CH2Cl2 / 120 h / 20 °C 3: 88 percent / aq. HCl / acetone; H2O / 48 h / 20 °C View Scheme

642-38-6

quebrachitol

D-1-O-cyclohexylcarbamoyl-2-deoxy-5,6-O-ethylidene-2-fluoro-3-O-methyl-chiro-inositol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethylaminosulfur trifluoride / CH2Cl2 / 4 h / 20 °C 2.1: 61 percent / 1,2-dichloro-ethane / 6 h / Heating 3.1: H2 / Raney-Nickel / ethanol / 8 h / 20 °C 3.2: triethylamine / ethanol / 8 h / 20 °C View Scheme

642-38-6

quebrachitol

D-1-O-cyclohexylcarbamoyl-2-deoxy-5,6-O-ethylidene-2-fluoro-3-O-methyl-chiro-inositol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethylaminosulfur trifluoride / CH2Cl2 / 4 h / 20 °C 2.1: 61 percent / 1,2-dichloro-ethane / 6 h / Heating 3.1: H2 / Raney-Nickel / ethanol / 8 h / 20 °C 3.2: triethylamine / ethanol / 8 h / 20 °C View Scheme

642-38-6

quebrachitol

D-5,6-O-(2-chloroethylidene)D-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-chiro-inositol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethylaminosulfur trifluoride / CH2Cl2 / 4 h / 20 °C 2.1: 61 percent / 1,2-dichloro-ethane / 6 h / Heating 3.1: H2 / Raney-Nickel / ethanol / 8 h / 20 °C 3.2: triethylamine / ethanol / 8 h / 20 °C View Scheme

642-38-6

quebrachitol

D-5,6-O-(2-chloroethylidene)-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-chiro-inositol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethylaminosulfur trifluoride / CH2Cl2 / 4 h / 20 °C 2.1: 61 percent / 1,2-dichloro-ethane / 6 h / Heating 3.1: H2 / Raney-Nickel / ethanol / 8 h / 20 °C 3.2: triethylamine / ethanol / 8 h / 20 °C View Scheme

L-QUEBRACHITOL Chemical Properties

L-QUEBRACHITOL Toxicity Data With Reference

L-QUEBRACHITOL Safety Profile

L-QUEBRACHITOL Specification