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111549-97-4

111549-97-4

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111549-97-4 Usage

General Description

5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol is a complex chemical compound that belongs to the category of organic substances known as O-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via an O-glycosidic bond. 5-O-Allyl-2,3,4-tri-O-benzyl-D-ribitol is specifically a sugar derivative, more precisely, a ribitol that has been substituted at various positions. The benzyl groups as substituents enhance the hydrophobic properties of the molecule, while the presence of allyl group can participate in a variety of chemical reactions, including oxidations, reductions, and cycloadditions. It is primarily used in the field of scientific research and is not generally found in natural sources.

Check Digit Verification of cas no

The CAS Registry Mumber 111549-97-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,1,5,4 and 9 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 111549-97:
(8*1)+(7*1)+(6*1)+(5*5)+(4*4)+(3*9)+(2*9)+(1*7)=114
114 % 10 = 4
So 111549-97-4 is a valid CAS Registry Number.
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

111549-97-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S,3S,4R)-2,3,4-tris(phenylmethoxy)-5-prop-2-enoxypentan-1-ol

1.2 Other means of identification

Product number -
Other names (2S,3S,4R)-5-(Allyloxy)-2,3,4-tris(benzyloxy)pentan-1-ol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:111549-97-4 SDS

111549-97-4Synthetic 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%
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

111549-97-4Downstream Products

111549-97-4Relevant articles and documents

Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them

-

Page column 20, (2010/02/07)

The present invention relates to the field of the Medicine, in particular with the chemical synthesis of oligosaccharide mixtures derived of ribose-ribitol-phosphate, which are used as active principle in vaccines for the prevention of infections caused byHaemophilus influenzaetype b (Hib), as well as with the vaccines containing said oligosaccharide mixtures. The oligasaccharide mixtures obtained by chemical synthesis of the present invention, comprise repeating units of formulae (phosphate-ribosa-ribitol)n or (ribose-ribitol-phosphate)n of at least 5 compounds of structure A or B, which represent the repeating unit of the capsular polysaccharide ofHaemophilus influenzaetype b and differ only by n, being n a value contained between 4 and 25 (n≧4 y≦25), and wherein R1or R2is a spacer for conjugation to a carrier, with the condition of R1=spacer if R2=H, or R2=spacer if R1=H. The invention also is related with the immunogens containing such oligosaccharide mixtures, with the vaccines containing said immunogens and with the methods to prepare these oligosaccharides as mixtures. Furthermore, the invention includes the use of the vaccines, alone or combined with other vaccines, for the prevention of the infections caused byHaemophilus influenzaetype b.

Synthese of oligomers of the capsular polysaccharide of the Haemophilus influenzae type b bacteria

Chan,Just

, p. 151 - 162 (2007/10/02)

-

A NEW APPROACH TO THE SYNTHESIS OF A DIMERIC FRAGMENT OF THE CAPSULAR POLYSACCHARIDE OF HAEMOPHILUS INFLUENZAE type b

Chan, Laval,Just, George

, p. 4049 - 4052 (2007/10/02)

The synthesis of the monomeric fragment of the Haemophilus influenzae type b (HIb) polysaccharide starting from orthoacetate 7 is described.The construction of the dimer is also reported.

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