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1,5-Anhydro-D-glucitol

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Name

1,5-Anhydro-D-glucitol

EINECS 205-829-3
CAS No. 154-58-5 Density 1.533 g/cm3
PSA 90.15000 LogP -2.53980
Solubility N/A Melting Point 142-143 °C
Formula C6H12O5 Boiling Point 376.8 °C at 760 mmHg
Molecular Weight 164.158 Flash Point 181.7 °C
Transport Information N/A Appearance White crystals
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 154-58-5 (1,5-Anhydro-D-glucitol) Hazard Symbols IrritantXi
Synonyms

D-Glucose,1-deoxy- (7CI);Glucitol, 1,5-anhydro-, D- (8CI);Polygalitol (6CI);1,5-Anhydroglucitol;1,5-Anhydrosorbitol;1-Deoxy-D-glucopyranose;Aceritol;

Article Data 65

1,5-Anhydro-D-glucitol Synthetic route

1338660-78-8

1,5-anhydro-2,3,4,6-tetra-O-allyl-D-glucitol

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
With methanol; palladium dichloride at 60℃; for 8h;100%
13137-69-4

1-deoxy-D-glucose tetraacetate

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
With sodium methylate In methanol at 45℃; for 0.333333h;98%
With sodium methylate In methanol at 20℃; for 16h;92%
With methanol; potassium carbonate at 25℃; for 1.5h;90%
19159-25-2

sucrose octakis(trimethylsilyl) ether

A

69-65-8

mannitol

B

50-70-4

D-sorbitol

C

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
Stage #1: sucrose octakis(trimethylsilyl) ether With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane In chloroform-d1 at 25℃; for 3h; Inert atmosphere; Glovebox;
Stage #2: In methanol Inert atmosphere; Glovebox;
A n/a
B n/a
C 90%

C32H72O6Si4

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 48h; Reagent/catalyst;86%
152840-34-1

1-deoxy-3,4,6-tri-O-benzyl-D-glucopyranose

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In methanol under 2327.2 Torr; for 4h;81%
2641-79-4

methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
Stage #1: methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane In chloroform-d1 at 25℃; for 1.5h; Inert atmosphere; Glovebox;
Stage #2: In methanol Inert atmosphere; Glovebox; regioselective reaction;
81%

(1R,2R,3S,4R,5R)-fluoro-2,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranoside

A

50-70-4

D-sorbitol

B

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
Stage #1: (1R,2R,3S,4R,5R)-fluoro-2,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranoside With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane In chloroform-d1 at 25℃; for 0.3h; Inert atmosphere; Glovebox;
Stage #2: In methanol Inert atmosphere; Glovebox; regioselective reaction;
A 9%
B 76%
19200-26-1

N,N-dimethyl β-D-glucopyranosyl dithiocarbamate

292638-85-8

acrylic acid methyl ester

A

methyl 3-(α-D-glucopyranosyl)propanoate

B

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In water at 75℃; for 1.5h; Reagent/catalyst; Inert atmosphere; stereoselective reaction;A 72%
B 28%
50-70-4

D-sorbitol

A

51607-79-5

2,5-anhydro-d-sorbitol

B

652-67-5

Isosorbide

C

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
With Amberlyst-15 at 120℃; under 7.50075 Torr; for 10h; Reagent/catalyst;A n/a
B 71%
C n/a

3,4,6-tri-O-tert-butyldimethylsilyl-1-deoxy-D-glucopyranose

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
With trifluoroacetic acid In methanol for 2.5h;70%

1,5-Anhydro-D-glucitol Specification

The CAS register number of 1,5-Anhydroglucitol is 154-58-5. It also can be called as D-Glucitol,1,5-anhydro- and the IUPAC name about this chemical is (2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol. The molecular formula about this chemical is C6H12O5 and the molecular weight is 164.15. It belongs to the following product categories which include 13C & 2H Sugars; Carbohydrates & Derivatives and so on.

Physical properties about 1,5-Anhydroglucitol are: (1)ACD/LogP: -1.24; (2)ACD/LogD (pH 5.5): -1.24; (3)ACD/LogD (pH 7.4): -1.24; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 5.06; (7)ACD/KOC (pH 7.4): 5.06; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 46.15Å2; (12)Index of Refraction: 1.58; (13)Molar Refractivity: 35.66 cm3; (14)Molar Volume: 107 cm3; (15)Polarizability: 14.13x10-24cm3; (16)Surface Tension: 66.8 dyne/cm; (17)Enthalpy of Vaporization: 72.24 kJ/mol; (18)Boiling Point: 376.8 °C at 760 mmHg; (19)Vapour Pressure: 3.21E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O[C@@H]1[C@H](OC[C@H](O)[C@H]1O)CO
(2)InChI: InChI=1/C6H12O5/c7-1-4-6(10)5(9)3(8)2-11-4/h3-10H,1-2H2/t3-,4+,5+,6+/m0/s1
(3)InChIKey: MPCAJMNYNOGXPB-SLPGGIOYBT
(4)Std. InChI: InChI=1S/C6H12O5/c7-1-4-6(10)5(9)3(8)2-11-4/h3-10H,1-2H2/t3-,4+,5+,6+/m0/s1
(5)Std. InChIKey: MPCAJMNYNOGXPB-SLPGGIOYSA-N

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