642-38-6

Usage

Chemical Properties

white to off-white powder

InChI:InChI=1/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1

Synthetic route

2-Methoxypropene (116-11-0) + quebrachitol (642-38-6) → 1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6)

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%

quebrachitol (642-38-6) → 1L-chiro-inositol (38876-99-2)

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

quebrachitol (642-38-6) + benzoyl chloride (98-88-4) → L-1,3,4,5,6-penta-O-benzoyl-2-O-methyl-chiro-inositol (73803-06-2)

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

quebrachitol (642-38-6) + 2,2-dimethoxy-propane (77-76-9) → 1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6) + 1L-5,6-O-Isopropyliden-2-O-methyl-chiro-inosit (17230-37-4)

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

cycloxexanone dimethyl ketal (933-40-4) + quebrachitol (642-38-6) → L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol (6848-53-9) + 1L-1,2-O-cyclohexylidene-5-O-methyl-chiro-inositol (754197-57-4)

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

quebrachitol (642-38-6) + benzyl bromide (100-39-0) → C42H44O6

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

quebrachitol (642-38-6) → (1S,2S,3R,4S,5S,6S)-1-fluoro-2-O-(methyl)cyclohexane-2,3,4,5,6-pentol (125290-99-5)

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;

quebrachitol (642-38-6) + benzoyl chloride (98-88-4) → C21H22O8 + C21H22O8 + C28H26O9 (341524-05-8)

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

quebrachitol (642-38-6) + benzoyl chloride (98-88-4) → L-1,3,4,5,6-penta-O-benzoyl-2-O-methyl-chiro-inositol (73803-06-2) + C28H26O9 (341524-05-8) + C35H30O10 (341524-06-9)

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

quebrachitol (642-38-6) → 3-deoxy-3-[18F]fluoro-O-methyl-myo-inositol

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

quebrachitol (642-38-6) → (1S)-1,3,4,5,6-penta-O-nitro-2-O-methyl-asymm.-inositol (28079-67-6, 134356-41-5)

Conditions	Yield
With sulfuric acid; nitric acid

quebrachitol (642-38-6) → chiro-inositol (18685-70-6)

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

chloro-trimethyl-silane (75-77-4) + quebrachitol (642-38-6) → (2S,3R,5R,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane (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)

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

1-ethoxycyclohexene (1122-84-5) + quebrachitol (642-38-6) → L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol (6848-53-9)

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

quebrachitol (642-38-6) → D-3-deoxy-3-fluoro-1-O-methyl-myo-inositol (125290-98-4) + (1S,2S,3R,4S,5S,6S)-1-fluoro-2-O-(methyl)cyclohexane-2,3,4,5,6-pentol (125290-99-5)

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

quebrachitol (642-38-6) + 2,2-dimethoxy-propane (77-76-9) → 1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6)

quebrachitol (642-38-6) + cyclohexanone (108-94-1) → L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol (6848-53-9)

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

quebrachitol (642-38-6) → bornesitol (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)

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

quebrachitol (642-38-6) → 3-O-Methyl-D-myo-inosose-(1) (3559-01-1, 5834-35-5, 20095-97-0, 92541-30-5, 92541-35-0, 92541-36-1)

Conditions	Yield
With oxygen; platinum on activated charcoal In water

hydrogenchloride (7647-01-0) + quebrachitol (642-38-6) + acetic acid (64-19-7) → chiro-inositol (18685-70-6)

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

quebrachitol (642-38-6) → 1L-1,2-di-O-methyl-chiro-inositol

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

quebrachitol (642-38-6) → 1L-3,4:5,6-di-O-cyclohexylidene-1,2-di-O-methyl-chiro-inositol (904689-58-3)

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

quebrachitol (642-38-6) → 1L-1-O-benzoyl-3,4:5,6-di-O-cyclohexylidene-2-O-methyl-chiro-inositol (60504-85-0, 128442-40-0, 131432-85-4, 131432-88-7)

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

quebrachitol (642-38-6) → 1-O-benzoyl-2-O-methyl-(-)-chiro-inositol (725273-54-1)

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

quebrachitol (642-38-6) → D-1-O-cyclohexylcarbamoyl-2-deoxy-5,6-O-ethylidene-2-fluoro-3-O-methyl-chiro-inositol

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

quebrachitol (642-38-6) → D-1-O-cyclohexylcarbamoyl-2-deoxy-5,6-O-ethylidene-2-fluoro-3-O-methyl-chiro-inositol

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

quebrachitol (642-38-6) → D-5,6-O-(2-chloroethylidene)D-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-chiro-inositol

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

quebrachitol (642-38-6) → D-5,6-O-(2-chloroethylidene)-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-chiro-inositol

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

Upstream product

• 87-89-8 D-myo-inositol 
• 77-78-1 dimethyl sulfate 
• 80971-02-4 (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol 
• 98906-25-3 (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 
• 58706-20-0 (+/-)-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 98906-26-4 (3aR,4R,5S,6S,7R,7aS)-5,6-Bis-allyloxy-4,7-bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 98906-29-7 (1R,2S,3R,4R,5S,6R)-2,4,5-Tris-allyloxy-3,6-bis-benzyloxy-cyclohexanol 
• 111446-91-4 (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol 
• 17793-95-2 cis-1,2-dihydrocatechol 
• 111015-71-5 (1α,2α,5β,6Sb)-5,6-epoxy-3-cyclohexene-1,2-diol dibenzoate 
• 111392-29-1 (3aS,4S,4aS,7aS,8S,8aR)-4-Allyloxy-8-methoxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 
• 86504-06-5 cis-3,5-cyclohexadiene-1,2-diol dibenzoate 
• 71-43-2 benzene 
• 98510-20-4 myo-Inositol orthoformate 

Downstream Products

• 54324-59-3 2,3,4,5,6-Penta-O-acetyl-1-O-methyl-myo-inositol 
• 14199-75-8 (1R,2S,3R,4R,5S,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane 
• 38876-99-2 1L-chiro-inositol 
• 28079-67-6 (1S)-1,3,4,5,6-penta-O-nitro-2-O-methyl-asymm.-inositol 
• 18685-70-6 chiro-inositol 
• 6848-53-9 L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol 
• 125290-98-4 D-3-deoxy-3-fluoro-1-O-methyl-myo-inositol 
• 125290-99-5 (1S,2S,3R,4S,5S,6S)-1-fluoro-2-O-(methyl)cyclohexane-2,3,4,5,6-pentol 
• 73803-06-2 L-1,3,4,5,6-penta-O-benzoyl-2-O-methyl-chiro-inositol 
• 484-68-4 bornesitol 
• 3559-01-1 3-O-Methyl-D-myo-inosose-⁽¹⁾ 
• 17230-42-1 3,4,5,6-Tetra-O-methyl-(-)-inosit; L-(1,2,4-3,5,6)-3,4,5,6-Tetramethoxy-1,2-cyclohexandiol 
• 117708-51-7 ((1R,2S,3S,4R,5S,6R)-2,3,4,5,6-Pentamethoxy-cyclohexyloxymethyl)-benzene 
• 157727-65-6 1-O-benzoyl-3,4:5,6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol 

Relevant academic research and scientific papers

Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis

Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.

Stereochemical observations on the bromate induced monobromopentahydroxylation of benzene by catalytic photoinduced charge transfer osmylation. A concise synthesis of (±)-pinitol

The use of lower temperatures in the title reaction favours the formation of the neo diastereoisomer of the deoxybromoinositol whose diisopropylidene derivative can be converted in three steps to (±)-pinitol.

An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics

Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

Approaches to the synthesis of glycosyl phosphatidyl inositols. Enantioselective synthesis of optically active chiro- and myo-inositols

An efficient synthetic strategy to optically active conveniently substituted D-chiro (5) and D-myo-inositol (10) derivatives has been developed starting from methyl α-D-glucopyranoside. Compounds 5 and 10 constitute valuable intermediates for the preparation of glycosyl phosphatidyl inositols.

Mikrobial Oxidation in Synthesis: Preparation of (+)- and (-)-Pinitol from Benzene

Microbial oxidation with Pseudomonas putida of benzene affords cis-1,2-dihydroxycyclohexa-3,5-diene (2) which may be converted in five steps and 49percent overall yield to (+/-)-pinitol.Resolution of an intermediate alcohol (6) with menthoxyacetyl chloride provides optically pure materials which may be independently transformed to (+)- or (-)-pinitol.Demethylation conditions for pinitol together with further reactions of (2) and related compounds were investigated.

MICROBIAL OXIDATION IN SYNTHESIS: A SIX STEP PREPARATION OF (+/-)-PINITOL FROM BENZENE

Synthesis of (+/-)-pinitol in 35percent overall yield from benzene has been achieved where the key step involved microbial oxidation of benzene to cis-1,2-dihydroxycyclohexa-3,5-diene.

The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates

Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.