Product Name

  • 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
  • Article Data26
  • CAS DataBase
  • Density 1.03 g/cm3
  • Solubility
  • Melting Point
  • Formula C13H24O5
  • Boiling Point 330.93 ºC at 760 mmHg
  • Molecular Weight 260.331
  • Flash Point 113 ºC
  • Transport Information
  • Appearance Colorless to light yellow liquid
  • Safety
  • Risk Codes
  • 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
  • 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;
  • PSA 64.99000
  • LogP 1.62070

Synthetic route

tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate
151140-38-4

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-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;
(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
154026-95-6

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

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

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-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 32℃; under 15201 Torr; for 16h;90%
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-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℃;
C18H32O6
1067638-10-1

C18H32O6

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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%
tert-butyl 2-((4R,6S)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
124655-08-9

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-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%
tert-butyl 2-((4R, 6S)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetate
143840-61-3

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

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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
isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate
147489-00-7

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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
isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate
147489-01-8

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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
isopropyl (2S,3S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-6-hydroxy-4-oxoheptanoate
147488-99-1

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h
2: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
4: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
5: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
2: 98 percent / p-TsOH / 2 h / Ambient temperature
3: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
4: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
5: NaBH4 / methanol / 0 °C
View Scheme
isopropyl (2S,3S)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dioxoheptanoate
147488-98-0

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 60 percent / DIBAL / tetrahydrofuran; hexane / 4 h / -78 °C
2: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h
3: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
4: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
5: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
6: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C
2: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
3: 98 percent / p-TsOH / 2 h / Ambient temperature
4: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
5: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
6: NaBH4 / methanol / 0 °C
View Scheme
tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 74 percent / NaH, n-BuLi / 20 h / -78 °C
2: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C
3: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
4: 98 percent / p-TsOH / 2 h / Ambient temperature
5: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
6: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
7: NaBH4 / methanol / 0 °C
View Scheme
(3R,5S)-3,5-Dihydroxy-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester
143827-05-8

(3R,5S)-3,5-Dihydroxy-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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: 81 percent / H(1+)
2: 1.) Bu3SnLi / 2.) Pd(PPh3)4
3: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
Multi-step reaction with 3 steps
1: 81 percent / H(1+)
2: 90 percent
3: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
(S)-5-Hydroxy-3-oxo-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester
143840-67-9

(S)-5-Hydroxy-3-oxo-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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: 60 percent / Et2BOMe, NaBH4
2: 81 percent / H(1+)
3: 1.) Bu3SnLi / 2.) Pd(PPh3)4
4: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
Multi-step reaction with 4 steps
1: 60 percent / Et2BOMe, NaBH4
2: 81 percent / H(1+)
3: 90 percent
4: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
[(4R,6S)-2,2-Dimethyl-6-((2S,3S)-3-trimethylsilanyl-oxiranyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester
143800-10-6

[(4R,6S)-2,2-Dimethyl-6-((2S,3S)-3-trimethylsilanyl-oxiranyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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: 1.) Bu3SnLi / 2.) Pd(PPh3)4
2: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
Multi-step reaction with 2 steps
1: 90 percent
2: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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: 100 percent / LDA / tetrahydrofuran / 1.75 h / -70 - -15 °C
2: 1). Et3B; 2.) NaBH4, MeOH / 1.) THF, 23 deg C, 15 min; 2.) -70 deg C
3: 70 percent / p-toluenesulfonic acid / acetone / 2 h / 23 °C
4: 80 percent / Bu4NF / tetrahydrofuran / 3 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
1.2: 2 h / 20 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
2.2: 6 h / 20 °C / Inert atmosphere
3.1: methanol; diethyl methoxy borane; sodium tetrahydroborate / tetrahydrofuran / 2.5 h / -80 - -70 °C / Inert atmosphere
4.1: methanesulfonic acid / 20 °C
5.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 750.08 - 1500.15 Torr / Autoclave
View Scheme
Multi-step reaction with 3 steps
1.1: (S)-5-benzyl 2,2,3-trimethyl-4-thione / ethanol / 0.5 h / 0 °C
1.2: 3 h / 0 - 30 °C
2.1: camphor-10-sulfonic acid / ethyl acetate / 4 h / 20 °C
3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h / 20 °C
View Scheme
(3R,5S)-tert-butyl 6-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexanoate
124655-07-8

(3R,5S)-tert-butyl 6-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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: 70 percent / p-toluenesulfonic acid / acetone / 2 h / 23 °C
2: 80 percent / Bu4NF / tetrahydrofuran / 3 h / 0 °C
View Scheme
(5S)-6-(tert-butyl-diphenylsilanyloxy)-5-hydroxy-3-oxohexanoic acid tert-butyl ester
124655-06-7

(5S)-6-(tert-butyl-diphenylsilanyloxy)-5-hydroxy-3-oxohexanoic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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: 1). Et3B; 2.) NaBH4, MeOH / 1.) THF, 23 deg C, 15 min; 2.) -70 deg C
2: 70 percent / p-toluenesulfonic acid / acetone / 2 h / 23 °C
3: 80 percent / Bu4NF / tetrahydrofuran / 3 h / 0 °C
View Scheme
1-methyl 6-tert.-butyl (2S,4R)-2,4-O-isopropylidene-2,4-dihydroxyadipate
140387-94-6

1-methyl 6-tert.-butyl (2S,4R)-2,4-O-isopropylidene-2,4-dihydroxyadipate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

Conditions
ConditionsYield
With hydrogenchloride; sodium borohydrid; ammonium chloride In tetrahydrofuran; methanol
With hydrogenchloride; sodium borohydrid; ammonium chloride In methanol
C13H25ClO4Si

C13H25ClO4Si

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 1 h / 0 °C
2.1: sodium tetrahydroborate / water / 14 h / 0 °C
3.1: acetone / 0.25 h / 25 °C
3.2: 6 h / 48 - 50 °C
4.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
5.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 1 h / 0 °C
2.1: diethyl methoxy borane / tetrahydrofuran; methanol / 1 h / 25 °C / Inert atmosphere
2.2: 4 h / -78 °C / Inert atmosphere
3.1: acetone / 0.25 h
3.2: 6 h / 48 - 50 °C
4.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
5.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 1 h / 0 °C
2.1: sodium tetrahydroborate; sodium dodecyl-sulfate / water / 14 h / 0 °C
3.1: acetone / 0.25 h
3.2: 6 h / 48 - 50 °C
4.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
5.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 5 steps
1: hydrogenchloride / water / 1 h / 0 °C
2: sodium tetrahydroborate / water / 14 h / 0 °C
3: (R)-10-camphorsulfonic acid / dichloromethane / 3 h / 40 °C
4: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
5: potassium carbonate; methanol / 0.5 h
View Scheme
(5S)-tert-butyl 6-chloro-3,5-dihydroxyhexanoate
406680-96-4

(5S)-tert-butyl 6-chloro-3,5-dihydroxyhexanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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
1.1: acetone / 0.25 h / 25 °C
1.2: 6 h / 48 - 50 °C
2.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
3.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: (R)-10-camphorsulfonic acid / dichloromethane / 3 h / 40 °C
2: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
3: potassium carbonate; methanol / 0.5 h
View Scheme
tert-butyl 2-((6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 85 °C
2: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water; dichloromethane / 24 h / 20 °C
2: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
3: potassium carbonate; methanol / 0.5 h
View Scheme
Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate
154026-92-3

Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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
1.1: sodium tetrahydroborate / water / 14 h / 0 °C
2.1: acetone / 0.25 h / 25 °C
2.2: 6 h / 48 - 50 °C
3.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
4.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 4 steps
1.1: diethyl methoxy borane / tetrahydrofuran; methanol / 1 h / 25 °C / Inert atmosphere
1.2: 4 h / -78 °C / Inert atmosphere
2.1: acetone / 0.25 h
2.2: 6 h / 48 - 50 °C
3.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
4.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate; sodium dodecyl-sulfate / water / 14 h / 0 °C
2.1: acetone / 0.25 h
2.2: 6 h / 48 - 50 °C
3.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
4.1: potassium carbonate; methanol / 0.5 h
View Scheme
1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate
154026-93-4

1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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
1.1: acetone / 0.25 h
1.2: 6 h / 48 - 50 °C
2.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
3.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: (1S)-10-camphorsulfonic acid / acetone / 6 h / 48 - 50 °C
2: 1-methyl-pyrrolidin-2-one / 24 h / 95 °C
3: methanol; potassium carbonate / 20 °C
View Scheme
tert-butyl 2-((6S)-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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: hydrogenchloride / water; dichloromethane / 48 h / 25 °C
2: potassium carbonate; methanol / 0.5 h
View Scheme
(4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester
154026-94-5

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

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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: 1-methyl-pyrrolidin-2-one / 24 h / 95 °C
2: methanol; potassium carbonate / 20 °C
View Scheme
tert-butyl (S)-4-(propylene oxide-2-yl)-3-oxobutanoate
623566-51-8

tert-butyl (S)-4-(propylene oxide-2-yl)-3-oxobutanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
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
1.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
1.2: 6 h / 20 °C / Inert atmosphere
2.1: methanol; diethyl methoxy borane; sodium tetrahydroborate / tetrahydrofuran / 2.5 h / -80 - -70 °C / Inert atmosphere
3.1: methanesulfonic acid / 20 °C
4.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 750.08 - 1500.15 Torr / Autoclave
View Scheme
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetic acid
154877-92-6

2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetic acid

Conditions
ConditionsYield
Stage #1: 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate With water; sodium hydroxide In methanol at 40 - 50℃;
Stage #2: With hydrogenchloride In water at 15 - 20℃; pH=4 - 4.2;		100%
With sodium hydroxide In tetrahydrofuran Reflux;
With sodium hydroxide In tetrahydrofuran Reflux;
1H-imidazole
288-32-4

1H-imidazole

ethyl acetate dichloromethane

ethyl acetate dichloromethane

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

(3R,5S)-6-iodo-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester
134742-42-0

(3R,5S)-6-iodo-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester

Conditions
ConditionsYield
With iodine; triphenylphosphine In benzene99%
...Expand
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

C13H24O5

C13H24O5

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetone at 50℃;99%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

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

Conditions
ConditionsYield
Swern oxidation; (further oxidizing agents);97%
Stage #1: 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate With dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 0℃; for 0.5h;
Stage #2: With pyridine; sulfur trioxide pyridine complex; dimethyl sulfoxide In dichloromethane at -5 - 20℃; for 1.16667h;		93%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In dichloromethane; water at 5 - 10℃; for 0.166667h; Temperature; Flow reactor;93.5%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(3R,5S)-6-<(methylsulfonyl)oxy>-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester
135054-68-1

(3R,5S)-6-<(methylsulfonyl)oxy>-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 0.5h;90%
With pyridine In dichloromethane; toluene
With triethylamine In dichloromethane100 g
C20H19FN2O3
906645-38-3

C20H19FN2O3

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

C33H41FN2O7
906645-40-7

C33H41FN2O7

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -5 - 20℃; Mitsunobu reaction;88%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

benzoyl chloride
98-88-4

benzoyl chloride

((4S,6R)-6-(2-tert-butoxy-2-oxoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)methyl benzoate
131666-50-7

((4S,6R)-6-(2-tert-butoxy-2-oxoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)methyl benzoate

Conditions
ConditionsYield
Stage #1: 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate With pyridine In dichloromethane at 20℃; for 0.5h;
Stage #2: benzoyl chloride In dichloromethane at 20℃; for 1h;		88%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

acetyl chloride
75-36-5

acetyl chloride

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
154026-95-6

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

Conditions
ConditionsYield
Stage #1: 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate With pyridine In dichloromethane at 20℃; for 0.5h;
Stage #2: acetyl chloride In dichloromethane at 20℃; for 1h;		86%
With pyridine In dichloromethane at 20℃; for 0.5h;15.9 g
2-methyl-2-phenylpropionic acid
826-55-1

2-methyl-2-phenylpropionic acid

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

C22H34O5

C22H34O5

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; tetrabutylammonium perchlorate; silver perchlorate In dichloromethane at 20℃; for 3h; Electrolysis; Molecular sieve;52%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

C17H28O6
707542-98-1

C17H28O6

Conditions
ConditionsYield
With manganese(IV) oxide In toluene for 17h; Heating / reflux;41%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

C40H44F2N2O5

C40H44F2N2O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / n-BuLi / 2 h / -78 - 25 °C
View Scheme
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

(6-{2-[3-(4-fluorophenyl)-1-isopropyl-5-(4-methoxybenzylcarbamoyl)-4-phenyl-1H-pyrrol-2-yl]vinyl}-2,2-dimethyl-[1,3]dioxan-4-yl)acetic acid tert-butyl ester
855249-03-5

(6-{2-[3-(4-fluorophenyl)-1-isopropyl-5-(4-methoxybenzylcarbamoyl)-4-phenyl-1H-pyrrol-2-yl]vinyl}-2,2-dimethyl-[1,3]dioxan-4-yl)acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / NaHMDS / tetrahydrofuran / 2 h / -78 - 25 °C
View Scheme
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

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

C42H51FN2O6

C42H51FN2O6

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 75 percent / NaHMDS / tetrahydrofuran / 2 h / -78 - 25 °C
2: hydrogen / Pd/C / methanol / 3 h / 25 °C / 2585.81 Torr
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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