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109428-30-0

109428-30-0

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109428-30-0 Usage

Uses

1,5:2,3-Dianhydro-4,6-O-benzylidene-D-allitol can be useful for synthesis of protected D-Altritol nucleosides as building blocks for oligonucleotide.

Check Digit Verification of cas no

The CAS Registry Mumber 109428-30-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,9,4,2 and 8 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 109428-30:
(8*1)+(7*0)+(6*9)+(5*4)+(4*2)+(3*8)+(2*3)+(1*0)=120
120 % 10 = 0
So 109428-30-0 is a valid CAS Registry Number.
InChI:InChI=1/C13H14O4/c1-2-4-8(5-3-1)13-15-6-9-11(17-13)12-10(16-12)7-14-9/h1-5,9-13H,6-7H2/t9?,10?,11-,12+,13?/m1/s1

109428-30-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name (7aR,7bS)-6-phenyl-1a,2,3a,4,7a,7b-hexahydrooxireno[1,2]pyrano[3,5-d][1,3]dioxine

1.2 Other means of identification

Product number -
Other names 1,5:2,3-Dianhydro-4,6-O-benzylidene-D-allitol

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:109428-30-0 SDS

109428-30-0Synthetic route

(4aR,8aS)-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine

(4aR,8aS)-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

Conditions
ConditionsYield
Stage #1: (4aR,8aS)-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h;
Stage #2: With dimethylsulfide for 0.166667h;		38%
4-Methyl-benzoic acid (4aR,7S,8R,8aR)-2-phenyl-8-(toluene-4-sulfonyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

4-Methyl-benzoic acid (4aR,7S,8R,8aR)-2-phenyl-8-(toluene-4-sulfonyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

Conditions
ConditionsYield
With sodium methylate In toluene at 50℃; Yield given;
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1,5-anhydro-2-azido-4,6-O-benzylidene-2-deoxy-D-altritol
921772-44-3

1,5-anhydro-2-azido-4,6-O-benzylidene-2-deoxy-D-altritol

Conditions
ConditionsYield
With sodium azide; ammonium chloride In 2-methoxy-ethanol; water at 100℃; for 18h;95%
With sodium azide; ammonium chloride In 2-methoxy-ethanol; water at 100℃; for 18h; Inert atmosphere;95%
uracil
66-22-8

uracil

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione
181711-37-5

1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 120℃;69%
Stage #1: uracil With sodium hydride In DMF (N,N-dimethyl-formamide) for 1h; Heating / reflux;
Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In DMF (N,N-dimethyl-formamide) for 24h; Heating / reflux;		29%
allylmagnesium bromide
2622-05-1

allylmagnesium bromide

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

(4aR,7R,8S,8aS)-7-allyl-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol

(4aR,7R,8S,8aS)-7-allyl-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol

Conditions
ConditionsYield
Stage #1: allylmagnesium bromide With copper(l) iodide In tetrahydrofuran at -30℃; for 0.25h; Inert atmosphere;
Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In tetrahydrofuran at -30℃; for 1.5h; Inert atmosphere; regioselective reaction;		69%
With copper(l) iodide In tetrahydrofuran at -30℃; for 1.5h; Inert atmosphere;69%
adenine
66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9

adenine

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

(4aR,7R,8S,8aS)-7-(6-Amino-purin-9-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
168696-01-3

(4aR,7R,8S,8aS)-7-(6-Amino-purin-9-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃;54%
thymin
65-71-4

thymin

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-5-methyl-1H-pyrimidine-2,4-dione

1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-5-methyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
Stage #1: thymin With sodium hydride In DMF (N,N-dimethyl-formamide) for 2h; Heating / reflux;
Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In DMF (N,N-dimethyl-formamide) for 24h; Heating / reflux;		47%
2-azidoethanol
1517-05-1

2-azidoethanol

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

(4aR,7R,8S,8aS)-7-(2-azidoethoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol

(4aR,7R,8S,8aS)-7-(2-azidoethoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol

Conditions
ConditionsYield
Stage #1: 2-azidoethanol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; Inert atmosphere;		45%
5-iodouracil
696-07-1

5-iodouracil

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-5-iodo-1H-pyrimidine-2,4-dione

1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-5-iodo-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
Stage #1: 5-iodouracil With sodium hydride In DMF (N,N-dimethyl-formamide) for 2h; Heating / reflux;
Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In DMF (N,N-dimethyl-formamide) for 24h; Heating / reflux;		20%
6-chloropurine
87-42-3

6-chloropurine

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

(4aR,7R,8S,8aS)-7-(6-Chloro-purin-9-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

(4aR,7R,8S,8aS)-7-(6-Chloro-purin-9-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;16%
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1,5-anhydro-2-azido-2-deoxy-D-altritol
921772-45-4

1,5-anhydro-2-azido-2-deoxy-D-altritol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / NaN3; NH4Cl / 2-methoxy-ethanol; H2O / 18 h / 100 °C
2: 66 percent / AcOH; water / 2 h / 95 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium azide; ammonium chloride / water; 2-methoxy-ethanol / 18 h / 100 °C / Inert atmosphere
2: acetic acid; water / 2 h / 95 °C
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1,5-anhydro-2-azido-2-deoxy-6-O-phosphono-D-altritol diammonium salt

1,5-anhydro-2-azido-2-deoxy-6-O-phosphono-D-altritol diammonium salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 95 percent / NaN3; NH4Cl / 2-methoxy-ethanol; H2O / 18 h / 100 °C
2.1: 66 percent / AcOH; water / 2 h / 95 °C
3.1: (MeO)3PO; POCl3 / 3 h / 0 °C
3.2: 46 percent / NH4OH; water / propan-2-ol
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

2-amino-1,5-anhydro-2-deoxy-6-O-phosphono-D-altritol sodium salt

2-amino-1,5-anhydro-2-deoxy-6-O-phosphono-D-altritol sodium salt

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 95 percent / NaN3; NH4Cl / 2-methoxy-ethanol; H2O / 18 h / 100 °C
2.1: 66 percent / AcOH; water / 2 h / 95 °C
3.1: (MeO)3PO; POCl3 / 3 h / 0 °C
3.2: 46 percent / NH4OH; water / propan-2-ol
4.1: H2; PtO2*H2O / H2O; methanol / 85 h / 20 °C / 1551.49 Torr
4.2: 91 percent / Dowex 50WX4-400 (Na+) / H2O
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1,5-anhydro-2-(3-carbamoylpyridinium)-2-deoxy-6-O-phosphono-D-altritol
921772-48-7

1,5-anhydro-2-(3-carbamoylpyridinium)-2-deoxy-6-O-phosphono-D-altritol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 95 percent / NaN3; NH4Cl / 2-methoxy-ethanol; H2O / 18 h / 100 °C
2.1: 66 percent / AcOH; water / 2 h / 95 °C
3.1: (MeO)3PO; POCl3 / 3 h / 0 °C
3.2: 46 percent / NH4OH; water / propan-2-ol
4.1: H2; PtO2*H2O / H2O; methanol / 85 h / 20 °C / 1551.49 Torr
4.2: 91 percent / Dowex 50WX4-400 (Na+) / H2O
5.1: 42 percent / Et3NH(+)HCO3(-) / methanol; H2O / 144 h / 40 °C
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

altritol nicotinamide adenine dinucleotide lithium salt

altritol nicotinamide adenine dinucleotide lithium salt

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 95 percent / NaN3; NH4Cl / 2-methoxy-ethanol; H2O / 18 h / 100 °C
2.1: 66 percent / AcOH; water / 2 h / 95 °C
3.1: (MeO)3PO; POCl3 / 3 h / 0 °C
3.2: 46 percent / NH4OH; water / propan-2-ol
4.1: H2; PtO2*H2O / H2O; methanol / 85 h / 20 °C / 1551.49 Torr
4.2: 91 percent / Dowex 50WX4-400 (Na+) / H2O
5.1: 42 percent / Et3NH(+)HCO3(-) / methanol; H2O / 144 h / 40 °C
6.1: AgNO3 / formamide; pyridine / 65 h / 20 °C
6.2: 39 percent / LiOH
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1,5-anhydro-3-O-benzoyl-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol
215959-65-2

1,5-anhydro-3-O-benzoyl-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
3: 70 percent / aq. CF3CO2H / 1 h
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

Benzoic acid (4aR,7R,8S,8aS)-7-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
215959-64-1

Benzoic acid (4aR,7R,8S,8aS)-7-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

N-[9-((4aR,7R,8S,8aS)-8-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-9H-purin-6-yl]-benzamide

N-[9-((4aR,7R,8S,8aS)-8-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-9H-purin-6-yl]-benzamide

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1,5-anhydro-3-O-benzoyl-2-deoxy-2-(N6-benzoyladenin-9-yl)-D-altro-hexitol
227079-12-1

1,5-anhydro-3-O-benzoyl-2-deoxy-2-(N6-benzoyladenin-9-yl)-D-altro-hexitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
4: aq. CF3CO2H / 1 h
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

Benzoic acid (4aR,7R,8S,8aS)-7-(6-benzoylamino-purin-9-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
227079-11-0

Benzoic acid (4aR,7R,8S,8aS)-7-(6-benzoylamino-purin-9-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1,5-anhydro-3-O-benzoyl-6-O-monomethoxytrityl-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol
215959-66-3

1,5-anhydro-3-O-benzoyl-6-O-monomethoxytrityl-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
3: 70 percent / aq. CF3CO2H / 1 h
4: 74 percent / AgNO3, 2,4,6-collidine / dimethylformamide
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1,5-anhydro-3-O-benzoyl-6-O-monomethoxytrityl-2-deoxy-2-(N6-benzoyladenin-9-yl)-D-altro-hexitol
227079-13-2

1,5-anhydro-3-O-benzoyl-6-O-monomethoxytrityl-2-deoxy-2-(N6-benzoyladenin-9-yl)-D-altro-hexitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
4: aq. CF3CO2H / 1 h
5: AgNO3, 2,4,6-collidine / dimethylformamide
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

2-(Uracil-1-yl)-3-O-benzoyl-2-deoxy-4-O-[N,N-diisopropyl(2-cyanoethyl)]phosphoramidite-6-O-monomethoxytrityl-D-altritol

2-(Uracil-1-yl)-3-O-benzoyl-2-deoxy-4-O-[N,N-diisopropyl(2-cyanoethyl)]phosphoramidite-6-O-monomethoxytrityl-D-altritol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
3: 70 percent / aq. CF3CO2H / 1 h
4: 74 percent / AgNO3, 2,4,6-collidine / dimethylformamide
5: 94 percent
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

2-(N6-Benzoyl-adenin-9-yl)-3-O-benzoyl-2-deoxy-4-O-[N,N-diisopropyl(2-cyanoethyl)]phosphoramidite-6-O-monomethoxytrityl-D-altritol

2-(N6-Benzoyl-adenin-9-yl)-3-O-benzoyl-2-deoxy-4-O-[N,N-diisopropyl(2-cyanoethyl)]phosphoramidite-6-O-monomethoxytrityl-D-altritol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
4: aq. CF3CO2H / 1 h
5: AgNO3, 2,4,6-collidine / dimethylformamide
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

4-Amino-1-((3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-1H-pyrimidin-2-one

4-Amino-1-((3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-1H-pyrimidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 69 percent / NaH / dimethylformamide / 120 °C
2: DMAP / pyridine / 83 h / Ambient temperature
3: NaOH / H2O; ethanol / 60 °C
4: pyridine / Ambient temperature
5: POCl3 / triethylamine; acetonitrile
6: NH3 / dioxane
7: H2O; acetic acid / 80 °C
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1-((3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-4-hydroxy-1H-pyrimidin-2-one

1-((3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-4-hydroxy-1H-pyrimidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 69 percent / NaH / dimethylformamide / 120 °C
2: DMAP / pyridine / 83 h / Ambient temperature
3: NaOH / H2O; ethanol / 60 °C
4: H2O; acetic acid / 80 °C
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1,5-anhydro-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol

1,5-anhydro-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 69 percent / NaH / dimethylformamide / 120 °C
2: 73 percent / H2O; acetic acid / 80 °C
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

1-((3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-4-hydroxy-5-iodo-1H-pyrimidin-2-one

1-((3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-4-hydroxy-5-iodo-1H-pyrimidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 69 percent / NaH / dimethylformamide / 120 °C
2: DMAP / pyridine / 83 h / Ambient temperature
3: NaOH / H2O; ethanol / 60 °C
4: pyridine / Ambient temperature
5: ICl / CH2Cl2 / Heating
6: 1.) NH3, 2.) H2O / 1.) MeOH, 2.) AcOH, 80 deg C
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

Acetic acid (4aR,7R,8R,8aS)-7-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
181711-39-7

Acetic acid (4aR,7R,8R,8aS)-7-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 69 percent / NaH / dimethylformamide / 120 °C
2: DMAP / pyridine / 83 h / Ambient temperature
3: NaOH / H2O; ethanol / 60 °C
4: pyridine / Ambient temperature
View Scheme
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
109428-30-0

1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol

Acetic acid (4aR,7R,8R,8aS)-7-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Acetic acid (4aR,7R,8R,8aS)-7-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 69 percent / NaH / dimethylformamide / 120 °C
2: DMAP / pyridine / 83 h / Ambient temperature
3: NaOH / H2O; ethanol / 60 °C
4: pyridine / Ambient temperature
5: POCl3 / triethylamine; acetonitrile
6: NH3 / dioxane
View Scheme

109428-30-0Upstream product

109428-30-0Relevant articles and documents

Synthesis of 1,5-anhydro-2-(N6-cyclopentyladenin-9-yl)-2-deoxy-D- altrohexitol

Verheggen,Van Aerschot,Pillet,Van der Wenden,Ijzerman,Herdewijn

, p. 321 - 324 (1995)

The N6-cyclopentyladenosine (CPA) analogue (4) was synthesized in 10 steps starting from glucose. The results of the radioligand binding assays are consistent with the thus far published findings that compounds containing a six-membered moiety at N9 exhibit extremely weak affinity for adenosine receptors. Replacement of the ribofuranosyl moiety of CPA (2) by a 2-deoxy-D-altrohexitol moiety is sufficient to completely abolish its agonist activity.

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