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CAS No.: | 13096-62-3 |
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Name: | 2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE |
Article Data: | 95 |
Molecular Structure: | |
Formula: | C34H34O6 |
Molecular Weight: | 538.64 |
Synonyms: | 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone; |
Density: | 1.22 g/cm3 |
Boiling Point: | 677.651 °C at 760 mmHg |
Flash Point: | 283.08 °C |
Hazard Symbols: | Xn |
Risk Codes: | 22 |
PSA: | 63.22000 |
LogP: | 5.88480 |
2,3,4,6-Tetra-O-benzyl-D-glucopyranose
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Solvent; | 100% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; | 100% |
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; | 100% |
2,3,4,6-tetra-O-benzyl-D-glucopyranoside
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With acetic anhydride; dimethyl sulfoxide at 20℃; | 93% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside In dimethyl sulfoxide at 20 - 25℃; for 0.5h; Inert atmosphere; Stage #2: With acetic anhydride at 15 - 25℃; Inert atmosphere; | 92% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h; | 82% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 105h; Stage #2: With triethylamine In dichloromethane at -78 - 20℃; for 1h; |
2,3,4,6-tetra-O-benzyl-D-glucopyranose
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With acetic anhydride In dimethyl sulfoxide at 20℃; | 89% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: With tetrapropylammonium perruthenate In dichloromethane at 20℃; for 2h; | 82% |
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h; | 82% |
(2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
Amberlite IR 120 H+ In 1,4-dioxane for 3h; Heating; | 88% |
2,3,4,6-tetra-O-benzoyl-D-glucopyranose
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Oxidation; | 85% |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With palladium diacetate In acetonitrile at 80℃; for 2h; | 60% |
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
In benzene for 5h; Ambient temperature; Irradiation; | A 57% B 24% |
phenacyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
In benzene for 5h; Ambient temperature; Irradiation; | A 56% B 20% |
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
B
2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone
Conditions | Yield |
---|---|
In toluene at 110℃; Inert atmosphere; | A 45% B 45% |
2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone
A
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
B
<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone
Conditions | Yield |
---|---|
With magnesium iodide In ethanol at 20℃; for 1h; | A 35% B 5% |
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The D-Gluconic acid,2,3,4,6-tetrakis-O-(phenylmethyl)-, d-lactone, with the CAS registry number of 13096-62-3, is also known as 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone. It belongs to the product category of Pharmaceutical Intermediates. Its molecular formula is C34H34O6 and molecular weight is 538.63016. What's more, its systematic name is (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one.
Physical properties about the D-Gluconic acid,2,3,4,6-tetrakis-O-(phenylmethyl)-, d-lactone are: (1)ACD/LogP: 6.11; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 8; (4)ACD/LogD (pH 7.4): 8; (5)ACD/BCF (pH 5.5): 448591; (6)ACD/BCF (pH 7.4): 448591; (7)ACD/KOC (pH 5.5): 386515; (8)ACD/KOC (pH 7.4): 386515; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 13; (12)Polar Surface Area: 63.22 Å2; (13)Index of Refraction: 1.614; (14)Molar Refractivity: 153.888 cm3; (15)Molar Volume: 441.363 cm3; (16)Surface Tension: 53.757 dyne/cm; (17)Density: 1.22 g/cm3; (18)Flash Point: 283.08 °C; (19)Enthalpy of Vaporization: 99.474 kJ/mol; (20)Boiling Point: 677.651 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C5O[C@H](COCc1ccccc1)[C@@H](OCc2ccccc2)[C@H](OCc3ccccc3)[C@H]5OCc4ccccc4
(2) InChI: InChI=1/C34H34O6/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-33H,21-25H2/t30-,31-,32+,33-/m1/s1
(3) InChIKey: BUBVLQDEIIUIQG-NXVJRICRBN