3,4-O-Isopropylidene-d-mannitol supplier

Name
3,4-O-ISOPROPYLIDENE-D-MANNITOL
EINECS
CAS No. 3969-84-4
Article Data35
CAS DataBase
Density 1.304 g/cm³
Solubility
Melting Point 85-88 °C(lit.)
Formula C₉H₁₈O₆
Boiling Point 438.8 °C at 760 mmHg
Molecular Weight 222.238
Flash Point 219.2 °C
Transport Information
Appearance White crystalline powder
Safety 22-24/25-36-26
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms Mannitol,3,4-O-isopropylidene- (6CI,7CI);Mannitol, 3,4-O-isopropylidene-, D- (8CI);3,4-Isopropylidene-D-mannitol;D-Mannitol3,4-acetonide;NSC 121512;
PSA 99.38000
LogP -1.78710

Synthetic route

: 3969-59-3, 4239-88-7, 81704-51-0
(+)-1,2,3,4,5,6-tris-O-isopropylidene-D-mannitol

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 3969-59-3
mannitol triacetonide

A: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

B: 38145-93-6
1,2:3,4-di-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With H-Beta zeolite; water In methanol at 20℃; for 6h; Product distribution; Further Variations:; Reagents; reaction time; molar ratio;	A 36% B 48%
With hydrogenchloride In ethanol at 45℃; for 1h;	A 36 % Chromat. B 42 % Chromat.
With hydrogenchloride In ethanol at 45℃; for 1h; Product distribution; time;	A 36 % Chromat. B 42 % Chromat.

: 69-65-8
mannitol

: 67-64-1
acetone

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
Stage #1: mannitol; acetone With sulfuric acid at 20℃; for 48h; Stage #2: With acetic acid In water for 2h; Further stages.;	38%
With sulfuric acid; acetic acid 1.) HOAc, 25 deg C, 20 h, 2.) 40 deg C, 1.75 h; Yield given. Multistep reaction;
With sulfuric acid; acetic acid 1.) 23 deg C, 24 h, 2.) 40 deg C, 2 h; Multistep reaction;
Stage #1: mannitol; acetone With sulfuric acid cyclocondensation; Stage #2: In water; acetic acid Hydrolysis; Further stages.;
Stage #1: mannitol; acetone With sulfuric acid cyclocondensation; Stage #2: With acetic acid at 40℃; for 2.5h; Hydrolysis; Further stages.;

: 64-19-7
acetic acid

: 3969-59-3
mannitol triacetonide

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

3.4-isopropylidene-1.6-dibenzoyl-d-mannitol: 3.4-isopropylidene-1.6-dibenzoyl-d-mannitol

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With ammonia at 20℃;

: 7732-18-5
water

: 63700-05-0
1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 69-65-8
mannitol

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With sodium carbonate; sulfuric acid In acetone
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / acetone / 24 h / Reflux 2: hydrogenchloride / water; methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: indium(III) triflate / 3 h / 65 °C 2: methanol / 2 h / 40 °C / Acidic conditions View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / acetone 2: acetic acid / water / 1 h / 40 °C View Scheme

: 18162-48-6
tert-butyldimethylsilyl chloride

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 172995-87-8
1,6-bis(tert-butyldimethylsilyloxy)-3,4-di-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 0℃; for 2h;	100%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;	100%
With dmap; triethylamine In dichloromethane at 20℃; for 8h;	94%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1.25h;

: 589-15-1
1-bromomethyl-4-bromobenzene

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 1,2,5,6-tetra-O-(4-bromobenzyl)-3,4-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
Stage #1: 3,4-di-O-isopropylidene-D-mannitol With 1H-imidazole; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromomethyl-4-bromobenzene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 24h; Inert atmosphere;	100%

: 100-39-0
benzyl bromide

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 20258-50-8
1,2,5,6-tetra-O-benzyl-3,4-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
Stage #1: 3,4-di-O-isopropylidene-D-mannitol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃;	98%
Stage #1: 3,4-di-O-isopropylidene-D-mannitol With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.75h; Inert atmosphere; Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;	93%
With sodium hydride In N,N-dimethyl-formamide
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 60℃;

: 76-83-5
trityl chloride

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 81841-56-7
O3,O4-isopropylidene-O1,O6-ditrityl-D-mannitol

Conditions

Conditions	Yield
With dmap In pyridine at 22℃; for 48h;	97%
With pyridine for 48h; Ambient temperature;	74%
With pyridine at 20℃; for 48h;

: 3282-30-2
pivaloyl chloride

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 1,6-dipivaloyl-3,4-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 24h;	95%

: 106-96-7
propargyl bromide

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: C21H26O6

Conditions

Conditions	Yield
Stage #1: 3,4-di-O-isopropylidene-D-mannitol With sodium hydride In N,N-dimethyl-formamide for 0.25h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene at 20℃; for 25h;	94%

: 1439-36-7
1-triphenylphosphoranylidene-2-propanone

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 1119511-32-8
(5R,6R)-5,6-dihydroxy-5,6-O-isopropylidene-deca-3,7-diene-2,9-dione

Conditions

Conditions	Yield
With sodium periodate; silica gel In dichloromethane at 20℃; for 20h; Wittig reaction;	92%

: 98-88-4
benzoyl chloride

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 51432-64-5
1,6-di-O-benzoyl-3,4-di-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With pyridine In dichloromethane at -80℃; for 4h;	90%
With pyridine In chloroform at 0℃;	80%
With pyridine In dichloromethane	72%

: 77-76-9
2,2-dimethoxy-propane

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 3969-59-3
mannitol triacetonide

Conditions

Conditions	Yield
In 1,2-dimethoxyethane for 48h; Heating;	89%

: 98-59-9
p-toluenesulfonyl chloride

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 53754-41-9
1,6-di-O-(p-toluenesulfonyl)-3,4-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With pyridine Tosylation;	86%
In pyridine at 0℃; for 3.75h;	84%
With pyridine

: 100-39-0
benzyl bromide

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 142285-64-1
1,6-di-O-benzyl-3,4-O-methylethylidene-D-mannitol

Conditions

Conditions	Yield
Stage #1: 3,4-di-O-isopropylidene-D-mannitol With di(n-butyl)tin oxide In toluene for 15h; Substitution; Heating; Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide In toluene at 70℃; for 15h; Substitution;	86%
Stage #1: 3,4-di-O-isopropylidene-D-mannitol With di(n-butyl)tin oxide In toluene Heating; Stage #2: benzyl bromide With cesium fluoride	82%
With di(n-butyl)tin oxide; cesium fluoride In hexane; N,N-dimethyl-formamide; toluene	65%
With di(n-butyl)tin oxide; cesium fluoride 1.) toluene; Yield given. Multistep reaction;

: 100-39-0
benzyl bromide

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 20196-69-4
1,2,5,6-tetra-O-benzyl-D-mannitol

Conditions

Conditions	Yield
With hydrogenchloride; acetyl chloride In methanol; hexane; N,N-dimethyl-formamide	81%
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil; N,N-dimethyl-formamide / 0.75 h / 0 - 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: acetic acid / water / 100 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 20 °C 2.1: hydrogenchloride / methanol; water / 4 h / Reflux View Scheme

: 100-44-7
benzyl chloride

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 20258-50-8
1,2,5,6-tetra-O-benzyl-3,4-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With sodium hydroxide; potassium carbonate; tert-Amyl alcohol; tetra(n-butyl)ammonium hydrogensulfate In dimethyl sulfoxide; benzene for 12h; Ambient temperature;	80%

: 98-59-9
p-toluenesulfonyl chloride

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: C37H42O14S4

Conditions

Conditions	Yield
With pyridine; triethylamine at 0 - 20℃; for 48h;	79%

: 103-71-9
phenyl isocyanate

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 110101-27-4
1,6-di-O-(phenylcarbmoyl)-3,4-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With Zn naphthenate; triethylamine In N,N-dimethyl-formamide for 1h; Ambient temperature;	77%

: 112-71-0
1-Bromotetradecane

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 128229-34-5
(4R,5R)-4,5-Bis-((R)-1,2-bis-tetradecyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 25℃; for 48h;	76%

: 459-46-1
4-Fluorobenzyl bromide

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 1,2,5,6-tetra-O-(4-fluorobenzyl)-D-mannitol

Conditions

Conditions	Yield
	73%

: 939-99-1
4-trifluoromethylbenzyl chloride

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 1,2,5,6-tetra-O-(4-trifluoromethylbenzyl)-D-mannitol

Conditions

Conditions	Yield
	72%

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 63700-05-0
1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate at 120℃; under 0.1 Torr; for 3h;	68%
Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / 4 h / 0 °C 2: K2CO3 / methanol / 2.5 h / 25 °C View Scheme

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 166239-53-8
(E)-3-[(4R,5R)-5-((E)-2-Ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid ethyl ester

Conditions

Conditions	Yield
With sodium periodate; silica gel In dichloromethane at 20℃; for 20h; Wittig reaction;	67%

: 104-81-4
4-Methylbenzyl bromide

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 1,2,5,6-tetra-O-(4-methylbenzyl)-D-mannitol

Conditions

Conditions	Yield
	65%

: 17201-43-3
4-cyanobenzyl bromide

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 1,2,5,6-tetra-O-(4-cyanobenzyl)-D-mannitol

Conditions

Conditions	Yield
	65%

: 76-83-5
trityl chloride

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 84608-23-1
3,4-O-isopropylidene-1-O-trityl-D-mannitol

Conditions

Conditions	Yield
With pyridine Ambient temperature;	63%

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 74044-75-0
(2R,3R,4R,5R)-3,4-O-(1-methylethylidene)-2,3,4,5-hexanetetraol

Conditions

Conditions	Yield
Stage #1: 3,4-di-O-isopropylidene-D-mannitol With pyridine; p-toluenesulfonyl chloride In dichloromethane at 0℃; for 4h; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Further stages.;	61%
Multi-step reaction with 2 steps 1: pyridine / 0 °C 2: LiAlH4 / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1: pyridine 2: K2CO3 / methanol 3: 85 percent / LiEt3BH / tetrahydrofuran / 2 h / 20 °C View Scheme

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: 74-88-4
methyl iodide

: 77049-48-0
3,4-O-isopropylidene-1,2,5,6-tetra-O-methyl-D-mannitol

Conditions

Conditions	Yield
With sodium methylsulfinylmethanide In dimethyl sulfoxide 1.) 0 degC, 2.) 0 degC to r.t.;	60%

: 3969-84-4
3,4-di-O-isopropylidene-D-mannitol

: C18H30O12P2

Conditions

Conditions	Yield
With Hexamethylphosphorous triamide In acetonitrile for 2h;	50%

3,4-O-Isopropylidene-d-mannitol Chemical Properties

IUPAC Name: (1S)-1-[(4R,5S)-5-[(1S)-1,2-Dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
Product Name: 3,4-O-Isopropylidene-d-mannitol
The MF of (1S)-1-[(4R,5S)-5-[(1S)-1,2-Dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (CAS NO.3969-84-4) is C₉H₁₈O₆.

The MW of (1S)-1-[(4R,5S)-5-[(1S)-1,2-Dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (CAS NO.3969-84-4) is 222.24.
Synonyms of (1S)-1-[(4R,5S)-5-[(1S)-1,2-Dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (CAS NO.3969-84-4): 3,4-Isopropylidene-D-mannitol ; 3,4-O-Isopropylidene-D-mannitol ; 3,4-Isopropylidene-D-mannitol , 98%
Product Categories: Biochemistry;Dioxanes & Dioxolanes;Dioxolanes;O-Substituted Sugars;Sugar Alcohols;Sugars;Naphthyridine,Quinoline;Carbohydrate Synthesis
Apperance: White crystalline powder
Index of Refraction: 1.509
Density: 1.303 g/ml
Flash Point: 219.2 °C
Boiling Point: 438.8 °C
Melting Point: 85-88 °C
Storage temp: Store at 0 °C

3,4-O-Isopropylidene-d-mannitol Uses

(1S)-1-[(4R,5S)-5-[(1S)-1,2-Dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (CAS NO.3969-84-4) is used as Chemical reagents, organic intermediates, fine chemicals, pharmaceutical research and development.

3,4-O-Isopropylidene-d-mannitol Safety Profile

Safety information of (1S)-1-[(4R,5S)-5-[(1S)-1,2-Dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (CAS NO.3969-84-4):
Hazard Codes Harmful Xn
Risk Statements
20/21/22 Harmful by inhalation, in contact with skin and if swallowed
36/37/38 Irritating to eyes, respiratory system and skin
Safety Statements
22 Do not breathe dust
24/25 Avoid contact with skin and eyes
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36 Wear suitable protective clothing
WGK Germany 3

Product Name

3,4-O-ISOPROPYLIDENE-D-MANNITOL

Synthetic route

3,4-O-Isopropylidene-d-mannitol Chemical Properties

3,4-O-Isopropylidene-d-mannitol Uses

3,4-O-Isopropylidene-d-mannitol Safety Profile

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