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5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol
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Name

5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol

 EINECS N/A
CAS No. 111549-97-4 Density 1.124g/cm3
PSA 57.15000 LogP 4.93750
Solubility N/A Melting Point N/A
Formula C29H34O5 Boiling Point 592.3 °C at 760 mmHg
Molecular Weight 462.586 Flash Point 312 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 111549-97-4 (5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol) Hazard Symbols N/A
Synonyms

D-Ribitol,2,3,4-tris-O-(phenylmethyl)-5-O-2-propenyl- (9CI);

Article Data 8

5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol Synthetic route

118964-50-4

5-O-allyl-2,3,4-tri-O-benzyl-D-ribose

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; water for 10h; Reduction;90%
With sodium tetrahydroborate In methanol Yield given;
111549-96-3

5-O-allyl-2,3,4-tri-O-benzyl-1-O-trityl-D-ribitol

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

Conditions
ConditionsYield
With water; acetic acid at 80℃; for 1.5h;90%
In water; acetic acid at 80℃; for 1.5h;90%
With water; acetic acid at 80℃; for 1.5h;
100-39-0

benzyl bromide

116490-75-6

5-O-allyl-2,3-di-O-benzyl-D-ribitol

A

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

B

116490-76-7

5-O-allyl-1,2,3-tri-O-benzyl-D-ribitol

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane for 16h; Heating;A 19%
B 56%
50-69-1

D-ribose

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 75 percent / conc. aq. HCl / 0.5 h / 0 °C
2.1: BuSnO23 / toluene / 4 h / Heating
2.2: 68 percent / CsF / dimethylformamide / 1 h / 20 °C
3.1: NaH / dimethylformamide / 0.5 h / 0 °C
3.2: 63 percent / dimethylformamide / 3.5 h / 0 °C
4.1: 86 percent / aq. HgCl2; CaCO3 / acetonitrile / 1 h / 20 °C
5.1: 90 percent / NaBH4 / methanol; H2O / 10 h
View Scheme
7152-47-8

D-ribose diethyl dithioacetal

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: BuSnO23 / toluene / 4 h / Heating
1.2: 68 percent / CsF / dimethylformamide / 1 h / 20 °C
2.1: NaH / dimethylformamide / 0.5 h / 0 °C
2.2: 63 percent / dimethylformamide / 3.5 h / 0 °C
3.1: 86 percent / aq. HgCl2; CaCO3 / acetonitrile / 1 h / 20 °C
4.1: 90 percent / NaBH4 / methanol; H2O / 10 h
View Scheme
129163-69-5

5-O-allyl D-ribose diethyl dithioacetal

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaH / dimethylformamide / 0.5 h / 0 °C
1.2: 63 percent / dimethylformamide / 3.5 h / 0 °C
2.1: 86 percent / aq. HgCl2; CaCO3 / acetonitrile / 1 h / 20 °C
3.1: 90 percent / NaBH4 / methanol; H2O / 10 h
View Scheme
Multi-step reaction with 3 steps
1: 91 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature
2: mercury(II)chloride, mercury(II)oxide / acetone; H2O / 2 h / Ambient temperature
3: sodium borohydride / methanol
View Scheme
118964-49-1

5-O-allyl 2,3,4-tri-O-benzyl-D-ribose diethyl dithioacetal

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / aq. HgCl2; CaCO3 / acetonitrile / 1 h / 20 °C
2: 90 percent / NaBH4 / methanol; H2O / 10 h
View Scheme
Multi-step reaction with 2 steps
1: mercury(II)chloride, mercury(II)oxide / acetone; H2O / 2 h / Ambient temperature
2: sodium borohydride / methanol
View Scheme
30725-00-9

2,3-O-isopropylidene-D-ribonic-γ-lactone

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 40 percent / silver oxide / dimethylformamide / 48 h / in dark
2: 80 percent / sodium borohydride / tetrahydrofuran / 55 °C / 2.) methanol 45 min and 1h
3: acetic acid; H2O / 4 h / 50 °C
4: pyridine / Ambient temperature
5: 86 percent / 1.) sodium hydride / dimethylformamide / 1.) 0 deg C 30 min; 2.) 0 deg C 30 min; 3.) room temperature overnight
6: 90 percent / acetic acid; H2O / 1.5 h / 80 °C
View Scheme
Multi-step reaction with 7 steps
1: 85 percent / pyridine / acetonitrile / 0 °C / 1.) 40 min; 2.) 1 h
2: LiAlH4, tetrakis(triphenylphosphine)palladium / dioxane / 0.25 h
3: 80 percent / sodium borohydride / tetrahydrofuran / 55 °C / 2.) methanol 45 min and 1h
4: acetic acid; H2O / 4 h / 50 °C
5: pyridine / Ambient temperature
6: 86 percent / 1.) sodium hydride / dimethylformamide / 1.) 0 deg C 30 min; 2.) 0 deg C 30 min; 3.) room temperature overnight
7: 90 percent / acetic acid; H2O / 1.5 h / 80 °C
View Scheme
Multi-step reaction with 6 steps
1: 85 percent / tetrahydrofuran; pyridine / 2 h / 0 °C
2: 100 percent / palladium tetrakis / dioxane / 0.25 h / Heating
3: 80 percent / NaBH4 / tetrahydrofuran; methanol / 2 h / 55 °C
4: 1.) HOAc, H2O / 1.) 50 degC, 4h 2.) pyridine, roomtemp., overnight
5: 86 percent / NaH / dimethylformamide / 1 h / 0 °C
6: 90 percent / HOAc, H2O / 1.5 h / 80 °C
View Scheme
111549-94-1

5-O-allyl-2,3-O-isopropylidene-D-ribitol

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; H2O / 4 h / 50 °C
2: pyridine / Ambient temperature
3: 86 percent / 1.) sodium hydride / dimethylformamide / 1.) 0 deg C 30 min; 2.) 0 deg C 30 min; 3.) room temperature overnight
4: 90 percent / acetic acid; H2O / 1.5 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: 1.) HOAc, H2O / 1.) 50 degC, 4h 2.) pyridine, roomtemp., overnight
2: 86 percent / NaH / dimethylformamide / 1 h / 0 °C
3: 90 percent / HOAc, H2O / 1.5 h / 80 °C
View Scheme
111549-93-0

5'-O-allyl-2',3'-O-isopropylidene-D-ribonic-γ-lactone

111549-97-4

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 80 percent / sodium borohydride / tetrahydrofuran / 55 °C / 2.) methanol 45 min and 1h
2: acetic acid; H2O / 4 h / 50 °C
3: pyridine / Ambient temperature
4: 86 percent / 1.) sodium hydride / dimethylformamide / 1.) 0 deg C 30 min; 2.) 0 deg C 30 min; 3.) room temperature overnight
5: 90 percent / acetic acid; H2O / 1.5 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1: 80 percent / NaBH4 / tetrahydrofuran; methanol / 2 h / 55 °C
2: 1.) HOAc, H2O / 1.) 50 degC, 4h 2.) pyridine, roomtemp., overnight
3: 86 percent / NaH / dimethylformamide / 1 h / 0 °C
4: 90 percent / HOAc, H2O / 1.5 h / 80 °C
View Scheme

5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol Specification

The 5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol, with CAS registry number 111549-97-4, has the systematic name of 2,3,4-tri-O-benzyl-5-O-prop-2-en-1-yl-D-ribitol. Besides this, it is also called D-ribitol, 2,3,4-tris-O-(phenylmethyl)-5-O-2-propen-1-yl-. And the chemical formula of this chemical is C29H34O5.

Physical properties of 5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol: (1)ACD/LogP: 7.12; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.12; (4)ACD/LogD (pH 7.4): 7.12; (5)ACD/BCF (pH 5.5): 151872.78; (6)ACD/BCF (pH 7.4): 151872.78; (7)ACD/KOC (pH 5.5): 178024.86; (8)ACD/KOC (pH 7.4): 178024.86; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 17; (12)Polar Surface Area: 46.15 Å2; (13)Index of Refraction: 1.568; (14)Molar Refractivity: 134.58 cm3; (15)Molar Volume: 411.3 cm3; (16)Polarizability: 53.35×10-24cm3; (17)Surface Tension: 44.5 dyne/cm; (18)Enthalpy of Vaporization: 92.89 kJ/mol; (19)Vapour Pressure: 7.12E-15 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O([C@@H]([C@@H](OCc1ccccc1)[C@@H](OCc2ccccc2)CO)COC\C=C)Cc3ccccc3
(2)InChI: InChI=1/C29H34O5/c1-2-18-31-23-28(33-21-25-14-8-4-9-15-25)29(34-22-26-16-10-5-11-17-26)27(19-30)32-20-24-12-6-3-7-13-24/h2-17,27-30H,1,18-23H2/t27-,28+,29-/m0/s1
(3)InChIKey: PBGRBWYIGUUVHW-NHKHRBQYBD
(4)Std. InChI: InChI=1S/C29H34O5/c1-2-18-31-23-28(33-21-25-14-8-4-9-15-25)29(34-22-26-16-10-5-11-17-26)27(19-30)32-20-24-12-6-3-7-13-24/h2-17,27-30H,1,18-23H2/t27-,28+,29-/m0/s1
(5)Std. InChIKey: PBGRBWYIGUUVHW-NHKHRBQYSA-N

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