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(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester
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Name

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester

 EINECS 432-960-5
CAS No. 124655-09-0 Density 1.03 g/cm3
PSA 64.99000 LogP 1.62070
Solubility N/A Melting Point N/A
Formula C13H24O5 Boiling Point 330.93 ºC at 760 mmHg
Molecular Weight 260.331 Flash Point 113 ºC
Transport Information N/A Appearance Colorless to light yellow liquid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 124655-09-0 ((4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester) Hazard Symbols N/A
Synonyms

((4R,6S)-6-Hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)aceticacid tert-butyl ester;(6S-Hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4R-yl)aceticacid tert-butyl ester;2-[(4R,6S)-6-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acidtert-butyl ester;tert-Butyl2-[(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetate;D-erythro-Hexonic acid,2,4-dideoxy-3,5-O-(1-methylethylidene)-, 1,1-dimethylethyl ester;

Article Data 26

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Synthetic route

151140-38-4

tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate at 31 - 33℃; under 7600 Torr; for 5h;100%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 750.075 - 1500.15 Torr; Autoclave;94%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 5h; Concentration;94%
With H2; palladium-carbon In ethyl acetate
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 25 - 30℃; under 7500.75 Torr; for 5h; Autoclave;
154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With potassium carbonate In methanol; water98%
With methanol; potassium carbonate for 0.5h;98%
With methanol; potassium carbonate at 20℃;92%

tert-butyl (3R,5S)-6-(4-methylbenzyloxy)-3,5-O-isopropylidene-3,5-dihydroxyhexanoate

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate at 32℃; under 15201 Torr; for 16h;90%
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 2h;83%
With sodium tetrahydroborate In methanol at 0℃;
1067638-10-1

C18H32O6

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 20℃; for 15h;81%
124655-08-9

tert-butyl 2-((4R,6S)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 3h;80%
143840-61-3

tert-butyl 2-((4R, 6S)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetate

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With sodium tetrahydroborate; ozone 1.) methanol; Yield given. Multistep reaction;

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
2: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
2: NaBH4 / methanol / 0 °C
View Scheme
147489-00-7

isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
2: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
3: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
4: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: 98 percent / p-TsOH / 2 h / Ambient temperature
2: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
3: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
4: NaBH4 / methanol / 0 °C
View Scheme
147489-01-8

isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
2: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
3: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
2: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
3: NaBH4 / methanol / 0 °C
View Scheme

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Chemical Properties

Molecular Structure of D-erythro-Hexonic acid,2,4-dideoxy-3,5-O-(1-methylethylidene)-, 1,1-dimethylethyl ester (CAS NO.124655-09-0):

Systematic Name: tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate 
Molecular Formula: C13H24O5
Molecular Weight: 260.33 
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 6
Index of Refraction: 1.442
Molar Refractivity: 66.806 cm3
Molar Volume: 252.655 cm3
Surface Tension: 35.469 dyne/cm
Density: 1.03 g/cm3
Flash Point: 113.122 °C
Enthalpy of Vaporization: 66.46 kJ/mol
Boiling Point: 330.93 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C
Appearance: Colorless to light yellow liquid
Product Categories: chiral; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals
SMILES: O=C(OC(C)(C)C)C[C@@H]1OC(O[C@@H](C1)CO)(C)C
InChI: InChI=1/C13H24O5/c1-12(2,3)18-11(15)7-9-6-10(8-14)17-13(4,5)16-9/h9-10,14H,6-8H2,1-5H3/t9-,10+/m1/s1
InChIKey: CFRUAOXMCVQMFP-ZJUUUORDBY

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Uses

D-erythro-Hexonic acid,2,4-dideoxy-3,5-O-(1-methylethylidene)-, 1,1-dimethylethyl ester (CAS NO.124655-09-0) is a useful synthetic intermediate.

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Specification

 D-erythro-Hexonic acid,2,4-dideoxy-3,5-O-(1-methylethylidene)-, 1,1-dimethylethyl ester (CAS NO.124655-09-0), its Synonyms are (4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester ; ((4R,6S)-6-Hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)acetic acid tert-butyl ester ; (6S-Hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4R-yl)acetic acid tert-butyl ester ; 2-[(4R,6S)-6-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert-butyl ester .

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