Product Name

  • Name

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

  • EINECS
  • CAS No. 111549-97-4
  • Article Data8
  • CAS DataBase
  • Density 1.124g/cm3
  • Solubility
  • Melting Point
  • Formula C29H34O5
  • Boiling Point 592.3 °C at 760 mmHg
  • Molecular Weight 462.586
  • Flash Point 312 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 111549-97-4 (5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol)
  • Hazard Symbols
  • Synonyms D-Ribitol,2,3,4-tris-O-(phenylmethyl)-5-O-2-propenyl- (9CI);
  • PSA 57.15000
  • LogP 4.93750

Synthetic route

5-O-allyl-2,3,4-tri-O-benzyl-D-ribose
118964-50-4

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

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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;
5-O-allyl-2,3,4-tri-O-benzyl-1-O-trityl-D-ribitol
111549-96-3

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

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-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;
benzyl bromide
100-39-0

benzyl bromide

5-O-allyl-2,3-di-O-benzyl-D-ribitol
116490-75-6

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

A

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

B

5-O-allyl-1,2,3-tri-O-benzyl-D-ribitol
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%
...Expand
D-ribose
50-69-1

D-ribose

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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
D-ribose diethyl dithioacetal
7152-47-8

D-ribose diethyl dithioacetal

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-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
1.1: 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
5-O-allyl D-ribose diethyl dithioacetal
129163-69-5

5-O-allyl D-ribose diethyl dithioacetal

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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
5-O-allyl 2,3,4-tri-O-benzyl-D-ribose diethyl dithioacetal
118964-49-1

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

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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
2,3-O-isopropylidene-D-ribonic-γ-lactone
30725-00-9

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

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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
5-O-allyl-2,3-O-isopropylidene-D-ribitol
111549-94-1

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

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-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
5'-O-allyl-2',3'-O-isopropylidene-D-ribonic-γ-lactone
111549-93-0

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

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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-(allyloxycarbonyl)-2,3-O-isopropylidene-D-ribonolactone
111549-92-9

5-O-(allyloxycarbonyl)-2,3-O-isopropylidene-D-ribonolactone

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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: LiAlH4, tetrakis(triphenylphosphine)palladium / dioxane / 0.25 h
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 5 steps
1: 100 percent / palladium tetrakis / dioxane / 0.25 h / Heating
2: 80 percent / NaBH4 / tetrahydrofuran; methanol / 2 h / 55 °C
3: 1.) HOAc, H2O / 1.) 50 degC, 4h 2.) pyridine, roomtemp., overnight
4: 86 percent / NaH / dimethylformamide / 1 h / 0 °C
5: 90 percent / HOAc, H2O / 1.5 h / 80 °C
View Scheme
5-O-allyl-1-O-trityl-D-ribitol
111549-95-2

5-O-allyl-1-O-trityl-D-ribitol

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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 / 1.) sodium hydride / dimethylformamide / 1.) 0 deg C 30 min; 2.) 0 deg C 30 min; 3.) room temperature overnight
2: 90 percent / acetic acid; H2O / 1.5 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: 86 percent / NaH / dimethylformamide / 1 h / 0 °C
2: 90 percent / HOAc, H2O / 1.5 h / 80 °C
View Scheme
(2S,3S,4R)-5-Allyloxy-pentane-1,2,3,4-tetraol

(2S,3S,4R)-5-Allyloxy-pentane-1,2,3,4-tetraol

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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: pyridine / Ambient temperature
2: 86 percent / 1.) sodium hydride / dimethylformamide / 1.) 0 deg C 30 min; 2.) 0 deg C 30 min; 3.) room temperature overnight
3: 90 percent / acetic acid; H2O / 1.5 h / 80 °C
View Scheme
D-Ribono-1,4-lactone
5336-08-3

D-Ribono-1,4-lactone

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) hydrochloric acid; 2.) pyridine / 1.) 24 h, room temperature; 2.) acetonitrile, 0 deg C 45 min and 0 deg C 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 7 steps
1: 95 percent / H(+) / 24 h / Ambient temperature
2: 85 percent / tetrahydrofuran; pyridine / 2 h / 0 °C
3: 100 percent / palladium tetrakis / dioxane / 0.25 h / Heating
4: 80 percent / NaBH4 / tetrahydrofuran; methanol / 2 h / 55 °C
5: 1.) HOAc, H2O / 1.) 50 degC, 4h 2.) pyridine, roomtemp., overnight
6: 86 percent / NaH / dimethylformamide / 1 h / 0 °C
7: 90 percent / HOAc, H2O / 1.5 h / 80 °C
View Scheme
β-5-O-allyl-1-O-methyl-2,3-O,O-isopropylidene-D-ribofuranoside
114488-50-5

β-5-O-allyl-1-O-methyl-2,3-O,O-isopropylidene-D-ribofuranoside

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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: 100 percent / aqueous 50percent trifluoroacetic acide / H2O; methanol / 8 h / Heating
2: 58 percent / pulverized potassium hydroxide / dimethylsulfoxide / Ambient temperature
3: 86 percent / 2M hydrochloric acid / dioxane / 8 h / Heating
4: 95 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
5: 19 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH2Cl2 / 16 h / Heating
View Scheme
Multi-step reaction with 5 steps
1: water, sulfuric acid / methanol / 2 h / Heating
2: 94 percent / zinc chloride / 0.25 h / Ambient temperature
3: 91 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature
4: mercury(II)chloride, mercury(II)oxide / acetone; H2O / 2 h / Ambient temperature
5: sodium borohydride / methanol
View Scheme
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
4099-85-8

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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: 87 percent / aqueous 50percent sodium hydroxide, tetrabutylammonium bromide / H2O / 6 h
2: 100 percent / aqueous 50percent trifluoroacetic acide / H2O; methanol / 8 h / Heating
3: 58 percent / pulverized potassium hydroxide / dimethylsulfoxide / Ambient temperature
4: 86 percent / 2M hydrochloric acid / dioxane / 8 h / Heating
5: 95 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
6: 19 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH2Cl2 / 16 h / Heating
View Scheme
Multi-step reaction with 6 steps
1: 97 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature
2: water, sulfuric acid / methanol / 2 h / Heating
3: 94 percent / zinc chloride / 0.25 h / Ambient temperature
4: 91 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature
5: mercury(II)chloride, mercury(II)oxide / acetone; H2O / 2 h / Ambient temperature
6: sodium borohydride / methanol
View Scheme
methyl 5-O-allyl-D-ribofuranoside
116490-68-7, 116490-69-8, 128775-32-6

methyl 5-O-allyl-D-ribofuranoside

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-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: 58 percent / pulverized potassium hydroxide / dimethylsulfoxide / Ambient temperature
2: 86 percent / 2M hydrochloric acid / dioxane / 8 h / Heating
3: 95 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
4: 19 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH2Cl2 / 16 h / Heating
View Scheme
5-O-allyl-2,3-di-O-benzyl-β-D-ribofuranose
329006-48-6

5-O-allyl-2,3-di-O-benzyl-β-D-ribofuranose

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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: 95 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
2: 19 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH2Cl2 / 16 h / Heating
View Scheme
(2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran
116490-72-3

(2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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: 86 percent / 2M hydrochloric acid / dioxane / 8 h / Heating
2: 95 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
3: 19 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH2Cl2 / 16 h / Heating
View Scheme
benzyl bromide
100-39-0

benzyl bromide

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
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 / NaH / dimethylformamide / 1 h / 0 °C
2: 90 percent / HOAc, H2O / 1.5 h / 80 °C
View Scheme
Methyl 5-O-allyl-D-ribofuranoside
116490-68-7, 116490-69-8, 128775-32-6

Methyl 5-O-allyl-D-ribofuranoside

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-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: 94 percent / zinc chloride / 0.25 h / Ambient temperature
2: 91 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature
3: mercury(II)chloride, mercury(II)oxide / acetone; H2O / 2 h / Ambient temperature
4: sodium borohydride / methanol
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

5-O-allyl-2,3,4-tri-O-benzyl-1-O-p-methoxybenzyl-D-ribitol
230620-30-1

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

Conditions
ConditionsYield
Stage #1: 2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Metallation;
Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 20℃; for 4h; Alkylation;		89%
O-(3-O-acetyl-2-azido-4-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-D-galactopyranosyl) trichloroacetimidate
1227612-68-1

O-(3-O-acetyl-2-azido-4-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-D-galactopyranosyl) trichloroacetimidate

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

5-O-allyl-2,3,4-tri-O-benzyl-1-O-(3-O-acetyl-2-azido-4-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-β-D-galactopyranosyl)-D-ribitol
1227613-04-8

5-O-allyl-2,3,4-tri-O-benzyl-1-O-(3-O-acetyl-2-azido-4-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-β-D-galactopyranosyl)-D-ribitol

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -40℃;88%
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -40℃; for 2h;81%
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
6974-32-9

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol
111549-98-5

5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 3h; Ambient temperature;85%
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve 1.) 1,2-dichloroethane, 90 min, room temperature; 2.) 1,2-dichloroethane, room temperature 2 h and 3 h; Yield given. Multistep reaction;
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

1,2-Di-O-acetyl-3-O-allyl-5-O-benzyl-α,β-D-ribofuranose

1,2-Di-O-acetyl-3-O-allyl-5-O-benzyl-α,β-D-ribofuranose

1-O-(2-O-Acetyl-3-O-allyl-5-O-benzyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol
118964-41-3

1-O-(2-O-Acetyl-3-O-allyl-5-O-benzyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane for 0.0833333h;81%
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

2,3,5-Tri-O-benzoyl-α,β-D-ribofuranosyl trichloroacetimidate

2,3,5-Tri-O-benzoyl-α,β-D-ribofuranosyl trichloroacetimidate

5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol
111549-98-5

5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane for 0.0833333h;81%
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

3-O-Allyl-2,5-di-O-benzoyl-β-D-ribofuranosyl trichloroacetimidate

3-O-Allyl-2,5-di-O-benzoyl-β-D-ribofuranosyl trichloroacetimidate

1-O-(3-O-Allyl-2,5-di-O-benzoyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol
158895-34-2

1-O-(3-O-Allyl-2,5-di-O-benzoyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol

Conditions
ConditionsYield
With 4 A molecular sieve; trimethylsilyl trifluoromethanesulfonate In dichloromethane 1.) r.t., 30 min, 2.) 0 deg C;80%
O-(2-deoxy-2-azido-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-galactopyranosyl)(1→3)-(2-deoxy-2-azido-4-O-benzyl-6-O-tert-butyldiphenylsilyl-α/β-D-galactopyranosyl) trichloroacetimidate

O-(2-deoxy-2-azido-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-galactopyranosyl)(1→3)-(2-deoxy-2-azido-4-O-benzyl-6-O-tert-butyldiphenylsilyl-α/β-D-galactopyranosyl) trichloroacetimidate

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

5-O-allyl-1-O-(3-O-[2-azido-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-galactopyranosyl]-2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-D-ribitol

5-O-allyl-1-O-(3-O-[2-azido-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-galactopyranosyl]-2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-galactopyranosyl)-2,3,4-tri-O-benzyl-D-ribitol

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -30 - 10℃; for 3h; Molecular sieve;74%
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

1,2,3,5-tetraacetylribose
13035-61-5

1,2,3,5-tetraacetylribose

1-O-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol
329006-50-0

1-O-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane for 0.25h;72%
Stage #1: 2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol With 4 A molecular sieve; boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 0 - 25℃;
Stage #2: 1,2,3,5-tetraacetylribose In 1,2-dichloro-ethane for 3.33333h;
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

2,3,5-Tri-O-acetyl-α,β-D-ribofuranosyl trichloroacetimidate

2,3,5-Tri-O-acetyl-α,β-D-ribofuranosyl trichloroacetimidate

1-O-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol
329006-50-0

1-O-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane for 0.0833333h;54%
Acetic acid (3R,4R,5R)-4-allyloxy-5-benzyloxymethyl-2-chloro-tetrahydro-furan-3-yl ester
124151-37-7

Acetic acid (3R,4R,5R)-4-allyloxy-5-benzyloxymethyl-2-chloro-tetrahydro-furan-3-yl ester

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

1-O-(2-O-Acetyl-3-O-allyl-5-O-benzyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol
118964-41-3

1-O-(2-O-Acetyl-3-O-allyl-5-O-benzyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol

Conditions
ConditionsYield
With molecular sieve; silver perchlorate In acetonitrile at -40℃; for 4h; Yield given;
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

Toluene-4-sulfonic acid (2S,3R,4R)-5-allyloxy-2,3,4-tris-benzyloxy-pentyl ester

Toluene-4-sulfonic acid (2S,3R,4R)-5-allyloxy-2,3,4-tris-benzyloxy-pentyl ester

Conditions
ConditionsYield
In pyridine Ambient temperature;
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

pivaloyl chloride
3282-30-2

pivaloyl chloride

5-O-allyl-2,3,4-tri-O-benzyl-1-O-pivaloyl-D-ribitol
909556-42-9

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

Conditions
ConditionsYield
With pyridine at 0 - 23℃; for 2h;
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

2-(aminoethyl)(1-D-ribityl) phosphate sodium salt

2-(aminoethyl)(1-D-ribityl) phosphate sodium salt

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: pyridine / 2 h / 0 - 23 °C
2.1: (1,5-cyclooctadiene)-bis(Me-diphenylphosphine)Ir F6phosphate / tetrahydrofuran / 4 h / 23 °C
3.1: 4.65 g / HgO; HgCl2 / acetone; H2O / 0.5 h / 23 °C
4.1: 85 percent / EtN(i-Pr)2 / acetonitrile / 1.5 h / 23 °C
5.1: 90 percent / NaOMe / dioxane; methanol / 72 h / 23 °C
6.1: 61 percent / EtN(i-Pr)2 / 1,2-dichloro-ethane / 2 h / 0 - 23 °C
7.1: tetrazole / acetonitrile / 1 h / 23 °C
7.2: 77 percent / pyridine; iodine / acetonitrile; tetrahydrofuran; H2O
8.1: 88 percent / HOAc; water / CH2Cl2 / 4 h / 23 °C
9.1: NH4OH / methanol / 8 h / Heating
9.2: Dowex 50 x 8-100 (Na(+)) / methanol
9.3: 88 percent / H2 / Pd/C / 2-methyl-propan-2-ol; H2O / 48 h / 23 °C / 10343 Torr
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

C13H25NO10P(1-)*Na(1+)

C13H25NO10P(1-)*Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: pyridine / 2 h / 0 - 23 °C
2.1: (1,5-cyclooctadiene)-bis(Me-diphenylphosphine)Ir F6phosphate / tetrahydrofuran / 4 h / 23 °C
3.1: 4.65 g / HgO; HgCl2 / acetone; H2O / 0.5 h / 23 °C
4.1: 85 percent / EtN(i-Pr)2 / acetonitrile / 1.5 h / 23 °C
5.1: 90 percent / NaOMe / dioxane; methanol / 72 h / 23 °C
6.1: 61 percent / EtN(i-Pr)2 / 1,2-dichloro-ethane / 2 h / 0 - 23 °C
7.1: tetrazole / acetonitrile / 1 h / 23 °C
7.2: 77 percent / pyridine; iodine / acetonitrile; tetrahydrofuran; H2O
8.1: 88 percent / HOAc; water / CH2Cl2 / 4 h / 23 °C
9.1: NH4OH / methanol / 8 h / Heating
9.2: Dowex 50 x 8-100 (Na(+)) / methanol
9.3: 88 percent / H2 / Pd/C / 2-methyl-propan-2-ol; H2O / 48 h / 23 °C / 10343 Torr
10.1: MeOH; Et3N / H2O / 23 °C
10.2: Dowex 50 x 8-100 (Na(+)) / H2O
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

2,3,4-tri-O-benzyl-1-O-pivaloyl-D-ribitol
909715-58-8

2,3,4-tri-O-benzyl-1-O-pivaloyl-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 2 h / 0 - 23 °C
2: (1,5-cyclooctadiene)-bis(Me-diphenylphosphine)Ir F6phosphate / tetrahydrofuran / 4 h / 23 °C
3: 4.65 g / HgO; HgCl2 / acetone; H2O / 0.5 h / 23 °C
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

2,3,4-tri-O-benzyl-1-O-pivaloyl-5-O-(propen-1-yl)-D-ribitol

2,3,4-tri-O-benzyl-1-O-pivaloyl-5-O-(propen-1-yl)-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 2 h / 0 - 23 °C
2: (1,5-cyclooctadiene)-bis(Me-diphenylphosphine)Ir F6phosphate / tetrahydrofuran / 4 h / 23 °C
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

2,3,4-tri-O-benzyl-5-O-(4,4'-dimethoxytrityl)-D-ribitol
909556-45-2

2,3,4-tri-O-benzyl-5-O-(4,4'-dimethoxytrityl)-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridine / 2 h / 0 - 23 °C
2: (1,5-cyclooctadiene)-bis(Me-diphenylphosphine)Ir F6phosphate / tetrahydrofuran / 4 h / 23 °C
3: 4.65 g / HgO; HgCl2 / acetone; H2O / 0.5 h / 23 °C
4: 85 percent / EtN(i-Pr)2 / acetonitrile / 1.5 h / 23 °C
5: 90 percent / NaOMe / dioxane; methanol / 72 h / 23 °C
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

[(N-benzyloxycarbonyl)-2-aminoethyl] 2-cyanoethyl (2,3,4-tri-O-benzyl-1-D-ribityl) phosphate
909556-48-5

[(N-benzyloxycarbonyl)-2-aminoethyl] 2-cyanoethyl (2,3,4-tri-O-benzyl-1-D-ribityl) phosphate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: pyridine / 2 h / 0 - 23 °C
2.1: (1,5-cyclooctadiene)-bis(Me-diphenylphosphine)Ir F6phosphate / tetrahydrofuran / 4 h / 23 °C
3.1: 4.65 g / HgO; HgCl2 / acetone; H2O / 0.5 h / 23 °C
4.1: 85 percent / EtN(i-Pr)2 / acetonitrile / 1.5 h / 23 °C
5.1: 90 percent / NaOMe / dioxane; methanol / 72 h / 23 °C
6.1: 61 percent / EtN(i-Pr)2 / 1,2-dichloro-ethane / 2 h / 0 - 23 °C
7.1: tetrazole / acetonitrile / 1 h / 23 °C
7.2: 77 percent / pyridine; iodine / acetonitrile; tetrahydrofuran; H2O
8.1: 88 percent / HOAc; water / CH2Cl2 / 4 h / 23 °C
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

2,3,4-tri-O-benzyl-5-O-(4,4'-dimethoxytrityl)-1-O-pivaloyl-D-ribitol
909556-44-1

2,3,4-tri-O-benzyl-5-O-(4,4'-dimethoxytrityl)-1-O-pivaloyl-D-ribitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 2 h / 0 - 23 °C
2: (1,5-cyclooctadiene)-bis(Me-diphenylphosphine)Ir F6phosphate / tetrahydrofuran / 4 h / 23 °C
3: 4.65 g / HgO; HgCl2 / acetone; H2O / 0.5 h / 23 °C
4: 85 percent / EtN(i-Pr)2 / acetonitrile / 1.5 h / 23 °C
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

2-cyanoethyl [2,3,4-tri-O-benzyl-5-O-(4,4'-dimethoxytrityl)-1-D-ribityl] N,N-diisopropylphosphoramidite
909556-46-3

2-cyanoethyl [2,3,4-tri-O-benzyl-5-O-(4,4'-dimethoxytrityl)-1-D-ribityl] N,N-diisopropylphosphoramidite

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: pyridine / 2 h / 0 - 23 °C
2: (1,5-cyclooctadiene)-bis(Me-diphenylphosphine)Ir F6phosphate / tetrahydrofuran / 4 h / 23 °C
3: 4.65 g / HgO; HgCl2 / acetone; H2O / 0.5 h / 23 °C
4: 85 percent / EtN(i-Pr)2 / acetonitrile / 1.5 h / 23 °C
5: 90 percent / NaOMe / dioxane; methanol / 72 h / 23 °C
6: 61 percent / EtN(i-Pr)2 / 1,2-dichloro-ethane / 2 h / 0 - 23 °C
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

[(N-benzyloxycarbonyl)-2-aminoethyl] 2-cyanoethyl [2,3,4-tri-O-benzyl-5-O-(4,4'-dimethoxytrityl)-1-D-ribityl] phosphate
909556-47-4

[(N-benzyloxycarbonyl)-2-aminoethyl] 2-cyanoethyl [2,3,4-tri-O-benzyl-5-O-(4,4'-dimethoxytrityl)-1-D-ribityl] phosphate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: pyridine / 2 h / 0 - 23 °C
2.1: (1,5-cyclooctadiene)-bis(Me-diphenylphosphine)Ir F6phosphate / tetrahydrofuran / 4 h / 23 °C
3.1: 4.65 g / HgO; HgCl2 / acetone; H2O / 0.5 h / 23 °C
4.1: 85 percent / EtN(i-Pr)2 / acetonitrile / 1.5 h / 23 °C
5.1: 90 percent / NaOMe / dioxane; methanol / 72 h / 23 °C
6.1: 61 percent / EtN(i-Pr)2 / 1,2-dichloro-ethane / 2 h / 0 - 23 °C
7.1: tetrazole / acetonitrile / 1 h / 23 °C
7.2: 77 percent / pyridine; iodine / acetonitrile; tetrahydrofuran; H2O
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

2,3,4-tri-O-benzyl-5-O-p-methoxybenzyl-L-ribitol
230635-00-4

2,3,4-tri-O-benzyl-5-O-p-methoxybenzyl-L-ribitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaH / dimethylformamide / 0.33 h / 0 °C
1.2: 89 percent / dimethylformamide / 4 h / 20 °C
2.1: 69 percent / 10 percent Pd/C / methanol; H2O / 10 h / 60 °C
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribitol
230620-43-6

1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaH / dimethylformamide / 0.33 h / 0 °C
1.2: 89 percent / dimethylformamide / 4 h / 20 °C
2.1: 69 percent / 10 percent Pd/C / methanol; H2O / 10 h / 60 °C
3.1: 16 percent / TMSOTf / acetonitrile / 0.67 h / -50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: NaH / dimethylformamide / 0.33 h / 0 °C
1.2: 89 percent / dimethylformamide / 4 h / 20 °C
2.1: 69 percent / 10 percent Pd/C / methanol; H2O / 10 h / 60 °C
3.1: 17 percent / TMSOTf / acetonitrile / 0.67 h / -50 °C
4.1: 63 percent / DDQ / CH2Cl2; H2O / 4 h
View Scheme
2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol
111549-97-4

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

1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 5-O-p-methoxybenzyl-2,3,4-tri-O-benzyl-L-ribitol
230620-42-5

1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 5-O-p-methoxybenzyl-2,3,4-tri-O-benzyl-L-ribitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaH / dimethylformamide / 0.33 h / 0 °C
1.2: 89 percent / dimethylformamide / 4 h / 20 °C
2.1: 69 percent / 10 percent Pd/C / methanol; H2O / 10 h / 60 °C
3.1: 17 percent / TMSOTf / acetonitrile / 0.67 h / -50 °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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