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(-)-2,3-O-Isopropylidene-D-threitol

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Name

(-)-2,3-O-Isopropylidene-D-threitol

EINECS 277-391-1
CAS No. 73346-74-4 Density 1.108 g/cm3
PSA 58.92000 LogP -0.50890
Solubility Soluble in water. Melting Point 48-51 °C(lit.)
Formula C7H14O4 Boiling Point 335.9 °C at 760 mmHg
Molecular Weight 162.186 Flash Point 111.9 °C
Transport Information N/A Appearance colorless to light yellow liquid
Safety 22-24/25-36-26 Risk Codes 20/21/22-36/37/38
Molecular Structure Molecular Structure of 73346-74-4 ((-)-2,3-O-Isopropylidene-D-threitol) Hazard Symbols HarmfulXn
Synonyms

1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-, (4R-trans)-;2,3-O-Isopropylidene-D-threitol;[(4R,5R)-5-Hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol;

Article Data 45

(-)-2,3-O-Isopropylidene-D-threitol Synthetic route

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate100%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1.25h;99%
With lithium aluminium tetrahydride In diethyl ether Reflux; Inert atmosphere;99%
73346-73-3

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran; ethanol at 20℃; for 14h;92%
With lithium aluminium tetrahydride84%
With lithium aluminium tetrahydride In diethyl ether for 16h; Heating;81%
81327-47-1

diisopropyl (2S,3S)-2,3-O-isopropylidenetartrate

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;90%

bis(1-methylethyl) (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;88%
126581-14-4

D-2,3-isopropylidene tartaric acid

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 16h; Inert atmosphere;85%
With sodium tetrahydroborate In ethyl [2]alcohol82%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;
59779-75-8

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride77.3%
3969-84-4

3,4-di-O-isopropylidene-D-mannitol

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lead(IV) acetate; nickel; ethyl acetate Hydrogenation;
With sodium tetrahydroborate; sodium periodate 1.) aq. acetone, 0 deg C, 2 h, 2.) O deg C, 1 h; Yield given. Multistep reaction;
With sodium tetrahydroborate; sodium periodate Yield given. Multistep reaction;
109715-58-4

(4R)-3,4-(isopropylidenedioxy)tetrahydrofuran-2-ol

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride
5754-27-8, 85362-89-6, 122137-20-6, 146566-82-7

(4S,5S)-2,2-dimethyl-[1,3]dioxolane-4,5-dicarbaldehyde

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In water; acetone at 15 - 20℃;
77-76-9

2,2-dimethoxy-propane

/PBAAB002-2250/

/PBAAB002-2250/

73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / p-TsOH / Heating
2: 87 percent / LiAlH4 / diethyl ether
View Scheme

(-)-2,3-O-Isopropylidene-D-threitol Specification

The (-)-2,3-O-Isopropylidene-D-threitol is an organic compound with the formula C7H14O4. The IUPAC name of this chemical is [(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol. With the CAS registry number 73346-74-4 and EINECS 277-391-1, it is also named as D-(-)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol. The product's categories are Heterocycles Series; Chiral; Chiral Reagents; Biochemistry; Chiral Building Blocks; Dioxanes & Dioxolanes; Dioxolanes; Glycidyl Compounds, etc. (Chiral); O-Substituted Sugars; Sugar Alcohols; Synthetic Organic Chemistry; Chiral Compound. It is colorless to light yellow liquid which should be sealed in the container and stored in the cool and dry place which must be away from oxidant.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.02; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 4; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 36.92 Å2; (7)Index of Refraction: 1.443; (8)Molar Refractivity: 38.82 cm3; (9)Molar Volume: 146.3 cm3; (10)Polarizability: 15.39×10-24 cm3; (11)Surface Tension: 42.8 dyne/cm; (12)Density: 1.108 g/cm3; (13)Flash Point: 111.9 °C; (14)Enthalpy of Vaporization: 67.09 kJ/mol; (15)Boiling Point: 335.9 °C at 760 mmHg; (16)Vapour Pressure: 8.03E-06 mmHg at 25°C.

Preparation of (-)-2,3-O-Isopropylidene-D-threitol: It can be obtained by (4S,5S)-4,5-bisethoxycarbonyl-2,2-dimethyl-1,3-dioxolane. This reaction needs reagent LiAlH4 and solvent diethyl ether by heating. The reaction time is 16 hours. The yield is 81%.

(-)-2,3-O-Isopropylidene-D-threitol can be obtained by (4S,5S)-4,5-bisethoxycarbonyl-2,2-dimethyl-1,3-dioxolane

Uses of (-)-2,3-O-Isopropylidene-D-threitol: It can react with toluene-4-sulfonyl chloride to get O2,O3-isopropylidene-O1,O4-bis-(toluene-4-sulfonyl)-D-threitol. This reaction needs reagent pyridine at temperature of -15 °C. The yield is 91%.

(-)-2,3-O-Isopropylidene-D-threitol can react with toluene-4-sulfonyl chloride to get O2,O3-isopropylidene-O1,O4-bis-(toluene-4-sulfonyl)-D-threitol

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure. 
1. SMILES:OC[C@H]1OC(O[C@@H]1CO)(C)C
2. InChI:InChI=1/C7H14O4/c1-7(2)10-5(3-8)6(4-9)11-7/h5-6,8-9H,3-4H2,1-2H3/t5-,6-/m1/s1
3. InChIKey:INVRLGIKFANLFP-PHDIDXHHBS

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