Product Name

  • Name

    (-)-2,3-O-Isopropylidene-D-threitol

  • EINECS 277-391-1
  • CAS No. 73346-74-4
  • Article Data45
  • CAS DataBase
  • Density 1.108 g/cm3
  • Solubility Soluble in water.
  • Melting Point 48-51 °C(lit.)
  • Formula C7H14O4
  • Boiling Point 335.9 °C at 760 mmHg
  • Molecular Weight 162.186
  • Flash Point 111.9 °C
  • Transport Information
  • Appearance colorless to light yellow liquid
  • Safety 22-24/25-36-26
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 73346-74-4 ((-)-2,3-O-Isopropylidene-D-threitol)
  • Hazard Symbols HarmfulXn
  • Synonyms 1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-, (4R-trans)-;2,3-O-Isopropylidene-D-threitol;[(4R,5R)-5-Hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol;
  • PSA 58.92000
  • LogP -0.50890

Synthetic route

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate
37031-29-1, 6134-82-3, 6135-80-4, 90613-41-5, 116499-08-2, 37031-30-4

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate100%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1.25h;99%
With lithium aluminium tetrahydride In diethyl ether Reflux; Inert atmosphere;99%
(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
73346-73-3

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran; ethanol at 20℃; for 14h;92%
With lithium aluminium tetrahydride84%
With lithium aluminium tetrahydride In diethyl ether for 16h; Heating;81%
diisopropyl (2S,3S)-2,3-O-isopropylidenetartrate
81327-47-1

diisopropyl (2S,3S)-2,3-O-isopropylidenetartrate

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;90%
bis(1-methylethyl) (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

bis(1-methylethyl) (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;88%
D-2,3-isopropylidene tartaric acid
126581-14-4

D-2,3-isopropylidene tartaric acid

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 16h; Inert atmosphere;85%
With sodium tetrahydroborate In ethyl [2]alcohol82%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;
diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
59779-75-8

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride77.3%
3,4-di-O-isopropylidene-D-mannitol
3969-84-4

3,4-di-O-isopropylidene-D-mannitol

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lead(IV) acetate; nickel; ethyl acetate Hydrogenation;
With sodium tetrahydroborate; sodium periodate 1.) aq. acetone, 0 deg C, 2 h, 2.) O deg C, 1 h; Yield given. Multistep reaction;
With sodium tetrahydroborate; sodium periodate Yield given. Multistep reaction;
(4R)-3,4-(isopropylidenedioxy)tetrahydrofuran-2-ol
109715-58-4

(4R)-3,4-(isopropylidenedioxy)tetrahydrofuran-2-ol

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride
(4S,5S)-2,2-dimethyl-[1,3]dioxolane-4,5-dicarbaldehyde
5754-27-8, 85362-89-6, 122137-20-6, 146566-82-7

(4S,5S)-2,2-dimethyl-[1,3]dioxolane-4,5-dicarbaldehyde

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In water; acetone at 15 - 20℃;
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

/PBAAB002-2250/

/PBAAB002-2250/

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / p-TsOH / Heating
2: 87 percent / LiAlH4 / diethyl ether
View Scheme
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

resin bound-Si(iPr2)-O-(CH2)3CHO

resin bound-Si(iPr2)-O-(CH2)3CHO

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / TsOH / cyclohexane; methanol / 52 - 54 °C
2: 82 percent / NaBH4 / ethanol / 2.5 h / 20 °C
View Scheme
mannitol triacetonide
3969-59-3

mannitol triacetonide

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70percent aq. CH3COOH / 1.5 h / 40 °C
2: 1.) sodium periodate, 2.) NaBH4 / 1.) aq. acetone, 0 deg C, 2 h, 2.) O deg C, 1 h
View Scheme
(+)-1,2,3,4,5,6-tris-O-isopropylidene-D-mannitol
3969-59-3, 4239-88-7, 81704-51-0

(+)-1,2,3,4,5,6-tris-O-isopropylidene-D-mannitol

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / aq. AcOH
2: 1) NaIO4; 2) sodium borohydride
View Scheme
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / methanol; cyclohexane / 0.25 h / 102 °C / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / methanol; cyclohexane / 7 h / 70 °C / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 23 °C / Inert atmosphere
View Scheme
methanol
67-56-1

methanol

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate
37031-29-1, 6134-82-3, 6135-80-4, 90613-41-5, 116499-08-2, 37031-30-4

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

Conditions
ConditionsYield
With sodium tetrahydroborate at 20℃; Cooling with ice;64.8 g
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

[(4R,5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
145554-06-9

[(4R,5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

Conditions
ConditionsYield
Stage #1: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol With sodium hydride In tetrahydrofuran; mineral oil at 5℃; for 0.75h; Inert atmosphere;
Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 20℃; for 16h; Inert atmosphere;		98%
Stage #1: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol With sodium hydride In 1,2-dimethoxyethane at 0℃; for 0.5h;
Stage #2: tert-butyldimethylsilyl chloride In 1,2-dimethoxyethane at 0 - 20℃;		97%
With sodium hydride In 1,2-dimethoxyethane at 0 - 20℃;97%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(4R,5R)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-hydroxymethyl-1,3-dioxolane
169871-36-7

(4R,5R)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-hydroxymethyl-1,3-dioxolane

Conditions
ConditionsYield
Stage #1: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: tert-butylchlorodiphenylsilane In tetrahydrofuran; mineral oil at 0℃; for 16h; Inert atmosphere;		96%
With sodium hydride 1.) THF, 45 min, RT, 2.) THF, 45 min; Yield given. Multistep reaction;
With sodium hydride In tetrahydrofuran
With sodium hydride
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

(2R,3R)-4-<(triisopropylsilyl)oxy>-2,3-(isopropylidenedioxy)butanol
221154-50-3

(2R,3R)-4-<(triisopropylsilyl)oxy>-2,3-(isopropylidenedioxy)butanol

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃; for 3h;96%
With sodium hydride In tetrahydrofuran at 20℃; for 3h;94%
With sodium hydride In tetrahydrofuran at 0 - 20℃;90%
With sodium hydride In tetrahydrofuran88%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

allyl bromide
106-95-6

allyl bromide

(4R,5R)-bis[(allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
783339-91-3

(4R,5R)-bis[(allyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
Stage #1: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 2h;		96%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

benzyl bromide
100-39-0

benzyl bromide

1,4-di-O-benzyl-2,3-O-isopropylidene-D-threitol
91604-40-9

1,4-di-O-benzyl-2,3-O-isopropylidene-D-threitol

Conditions
ConditionsYield
Stage #1: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol With sodium hydride In tetrahydrofuran at 20 - 80℃; for 2h;
Stage #2: benzyl bromide In tetrahydrofuran at 80℃; for 24h;		95%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

10-bromo-5,15-diphenylporphyrin

10-bromo-5,15-diphenylporphyrin

C71H54N8O4

C71H54N8O4

Conditions
ConditionsYield
With caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 36h;95%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

C23H30O6

C23H30O6

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h;93%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

1,4-di-o-tosyl-2,3-isopropylidene-D-threitol
51064-65-4

1,4-di-o-tosyl-2,3-isopropylidene-D-threitol

Conditions
ConditionsYield
With pyridine at -15℃;91%
With triethylamine In diethyl ether at 30℃; for 17h;85%
With triethylamine In tert-butyl methyl ether85%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(4R,5R)-<5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-yl>methyl p-toluenesulfonate
73711-65-6

(4R,5R)-<5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-yl>methyl p-toluenesulfonate

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 20℃; for 2h; Inert atmosphere;91%
With n-butyllithium89%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane; water at 0 - 20℃; for 1h;73.3%
With n-butyllithium DMSO, THF, 1) r.t., 15 min, 2) r.t., 1 h; Yield given. Multistep reaction;
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

6-benzyloxyhexyl 4-methylbenzenesulfonate
126519-80-0

6-benzyloxyhexyl 4-methylbenzenesulfonate

1,4-bis-O-(6-benzyloxyhexyl)-2,3-O-isopropylidene-D-threitol
866429-85-8

1,4-bis-O-(6-benzyloxyhexyl)-2,3-O-isopropylidene-D-threitol

Conditions
ConditionsYield
Stage #1: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol With sodium hydride In tetrahydrofuran at 20 - 80℃; for 2h;
Stage #2: 6-benzyloxyhexyl 4-methylbenzenesulfonate In tetrahydrofuran at 80℃; for 72h;		91%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

benzyl bromide
100-39-0

benzyl bromide

1-O-benzyl-2,3-O-isopropylidene-D-threitol
78469-77-9

1-O-benzyl-2,3-O-isopropylidene-D-threitol

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 2h; from -50 deg C to 0 deg C;89%
With sodium hydride In N,N-dimethyl-formamide88%
With sodium hydride In N,N-dimethyl-formamide 1.) -15 deg C, 30 min, 2.) -15 deg C, 0.5 h; r.t. 1 h;86%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

benzyl chloride
100-44-7

benzyl chloride

1-O-benzyl-2,3-O-isopropylidene-D-threitol
78469-77-9

1-O-benzyl-2,3-O-isopropylidene-D-threitol

Conditions
ConditionsYield
Stage #1: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol With sodium hydride In N,N-dimethyl-formamide at -15℃; for 0.5h;
Stage #2: benzyl chloride In N,N-dimethyl-formamide at 20℃; for 1h;		88%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 50℃; for 14h;74%
With sodium hydroxide 1.) DMSO, RT, 1 h, 2.) DMSO, 12 h; Yield given; Multistep reaction;
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester
1822-66-8

3,4-dihydroxythiophene-2,5-dicarboxylic acid diethyl ester

C17H22O8S
1311140-79-0

C17H22O8S

Conditions
ConditionsYield
With tributylphosphine; diamide In tetrahydrofuran at 60℃; Mitsunobu reaction; Darkness; Inert atmosphere;86%
With tributylphosphine; diamide In tetrahydrofuran at 60℃; for 36h; Mitsunobu reaction;78%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

((4R,5R)-5-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol
118620-86-3

((4R,5R)-5-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

Conditions
ConditionsYield
With 85percent KOH In benzene for 9h; Heating;83%
With potassium hydroxide In benzene for 9h; Inert atmosphere; Reflux;82%
Stage #1: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol With sodium hydride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;
Stage #2: p-methoxybenzyl chloride In tetrahydrofuran at 23℃; Inert atmosphere;		78%
Stage #1: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 1.5h;
Stage #2: p-methoxybenzyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 18h;		74%
With potassium hydroxide In benzene for 4h; Heating;73%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

threitol
2319-57-5

threitol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h;83%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2,3-O-isopropylidene-1,4-di-O-methanesulphonyl-D-threitol
109281-59-6

2,3-O-isopropylidene-1,4-di-O-methanesulphonyl-D-threitol

Conditions
ConditionsYield
With pyridine In dichloromethane82%
With pyridine66%
With pyridine
With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere;
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

benzyl chloride
100-44-7

benzyl chloride

1,4-di-O-benzyl-2,3-O-isopropylidene-D-threitol
91604-40-9

1,4-di-O-benzyl-2,3-O-isopropylidene-D-threitol

Conditions
ConditionsYield
With paraffine; sodium hydride In tetrahydrofuran 1.) 16 h, RT, 2.) 2 h, reflux;81%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

ethyl chlorocarbonylacetate
36239-09-5

ethyl chlorocarbonylacetate

Malonic acid (4R,5R)-5-(2-ethoxycarbonyl-acetoxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester ethyl ester
200133-32-0

Malonic acid (4R,5R)-5-(2-ethoxycarbonyl-acetoxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester ethyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane for 5h; Ambient temperature;81%
With pyridine In dichloromethane Yield given;
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

(Z)-(4R,5R)-3-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)acrylic acid methyl ester
109613-69-6

(Z)-(4R,5R)-3-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)acrylic acid methyl ester

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane at 20℃; for 24h; stereoselective reaction;80%
(3aS)-1-chloro-2-phenyl-hexahydro-1H-pyrrolo[1,2-c][1,3,2]diazaphosphole

(3aS)-1-chloro-2-phenyl-hexahydro-1H-pyrrolo[1,2-c][1,3,2]diazaphosphole

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

(4R,5R)-4,5-bis[((2R,5S)-3-phenyl-1,3-diaza-2-phosphabicyclo[3.3.0]octyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

(4R,5R)-4,5-bis[((2R,5S)-3-phenyl-1,3-diaza-2-phosphabicyclo[3.3.0]octyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20 - 45℃; for 24.5h; Inert atmosphere; stereoselective reaction;80%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

benzyl bromide
100-39-0

benzyl bromide

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane
78469-77-9, 81076-11-1, 128820-40-6, 78513-03-8

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
With silver(l) oxide In toluene at 20℃; for 8h; Inert atmosphere;77%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

ethyl chlorocarbonylacetate
36239-09-5

ethyl chlorocarbonylacetate

C12H20O7
1433901-15-5

C12H20O7

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;77%
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

propargyl bromide
106-96-7

propargyl bromide

C13H18O4

C13H18O4

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h;71%
triethylsilyl chloride
994-30-9

triethylsilyl chloride

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol
73346-74-4

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

((4R,5R)-2,2-Dimethyl-5-(triethylsilyloxymethyl)-1,3-dioxolan-4-yl)methanol

((4R,5R)-2,2-Dimethyl-5-(triethylsilyloxymethyl)-1,3-dioxolan-4-yl)methanol

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 3h; Inert atmosphere;70%

(-)-2,3-O-Isopropylidene-D-threitol Specification

The (-)-2,3-O-Isopropylidene-D-threitol is an organic compound with the formula C7H14O4. The IUPAC name of this chemical is [(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol. With the CAS registry number 73346-74-4 and EINECS 277-391-1, it is also named as D-(-)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol. The product's categories are Heterocycles Series; Chiral; Chiral Reagents; Biochemistry; Chiral Building Blocks; Dioxanes & Dioxolanes; Dioxolanes; Glycidyl Compounds, etc. (Chiral); O-Substituted Sugars; Sugar Alcohols; Synthetic Organic Chemistry; Chiral Compound. It is colorless to light yellow liquid which should be sealed in the container and stored in the cool and dry place which must be away from oxidant.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.02; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 4; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 36.92 Å2; (7)Index of Refraction: 1.443; (8)Molar Refractivity: 38.82 cm3; (9)Molar Volume: 146.3 cm3; (10)Polarizability: 15.39×10-24 cm3; (11)Surface Tension: 42.8 dyne/cm; (12)Density: 1.108 g/cm3; (13)Flash Point: 111.9 °C; (14)Enthalpy of Vaporization: 67.09 kJ/mol; (15)Boiling Point: 335.9 °C at 760 mmHg; (16)Vapour Pressure: 8.03E-06 mmHg at 25°C.

Preparation of (-)-2,3-O-Isopropylidene-D-threitol: It can be obtained by (4S,5S)-4,5-bisethoxycarbonyl-2,2-dimethyl-1,3-dioxolane. This reaction needs reagent LiAlH4 and solvent diethyl ether by heating. The reaction time is 16 hours. The yield is 81%.

(-)-2,3-O-Isopropylidene-D-threitol can be obtained by (4S,5S)-4,5-bisethoxycarbonyl-2,2-dimethyl-1,3-dioxolane

Uses of (-)-2,3-O-Isopropylidene-D-threitol: It can react with toluene-4-sulfonyl chloride to get O2,O3-isopropylidene-O1,O4-bis-(toluene-4-sulfonyl)-D-threitol. This reaction needs reagent pyridine at temperature of -15 °C. The yield is 91%.

(-)-2,3-O-Isopropylidene-D-threitol can react with toluene-4-sulfonyl chloride to get O2,O3-isopropylidene-O1,O4-bis-(toluene-4-sulfonyl)-D-threitol

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure. 
1. SMILES:OC[C@H]1OC(O[C@@H]1CO)(C)C
2. InChI:InChI=1/C7H14O4/c1-7(2)10-5(3-8)6(4-9)11-7/h5-6,8-9H,3-4H2,1-2H3/t5-,6-/m1/s1
3. InChIKey:INVRLGIKFANLFP-PHDIDXHHBS

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