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3,4-O-ISOPROPYLIDENE-D-MANNITOL is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

3969-84-4

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3969-84-4 Usage

Chemical Properties

White crystalline powder

Check Digit Verification of cas no

The CAS Registry Mumber 3969-84-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,9,6 and 9 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3969-84:
(6*3)+(5*9)+(4*6)+(3*9)+(2*8)+(1*4)=134
134 % 10 = 4
So 3969-84-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H18O6/c1-9(2)14-7(5(12)3-10)8(15-9)6(13)4-11/h5-8,10-13H,3-4H2,1-2H3/t5-,6-,7-,8-/m1/s1

3969-84-4 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • TCI America

  • (I0489)  3,4-O-Isopropylidene-D-mannitol  >96.0%(GC)

  • 3969-84-4

  • 1g

  • 630.00CNY

  • Detail
  • TCI America

  • (I0489)  3,4-O-Isopropylidene-D-mannitol  >96.0%(GC)

  • 3969-84-4

  • 5g

  • 1,950.00CNY

  • Detail
  • Alfa Aesar

  • (B21070)  3,4-O-Isopropylidene-D-mannitol, 97%   

  • 3969-84-4

  • 1g

  • 468.0CNY

  • Detail
  • Alfa Aesar

  • (B21070)  3,4-O-Isopropylidene-D-mannitol, 97%   

  • 3969-84-4

  • 5g

  • 1400.0CNY

  • Detail
  • Aldrich

  • (338176)  3,4-O-Isopropylidene-D-mannitol  97%

  • 3969-84-4

  • 338176-5G

  • 1,330.29CNY

  • Detail

3969-84-4Synthetic route

(+)-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

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

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

mannitol triacetonide
3969-59-3

mannitol triacetonide

A

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

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

B

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

1,2:3,4-di-O-isopropylidene-D-mannitol

Conditions
ConditionsYield
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.
mannitol
69-65-8

mannitol

acetone
67-64-1

acetone

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

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

Conditions
ConditionsYield
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.;
acetic acid
64-19-7

acetic acid

mannitol triacetonide
3969-59-3

mannitol triacetonide

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

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

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

Conditions
ConditionsYield
With ammonia at 20℃;
water
7732-18-5

water

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

1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol

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

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

mannitol
69-65-8

mannitol

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

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

Conditions
ConditionsYield
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
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

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

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

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

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

Conditions
ConditionsYield
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;
1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

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

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

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

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

Conditions
ConditionsYield
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%
benzyl bromide
100-39-0

benzyl bromide

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

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

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

1,2,5,6-tetra-O-benzyl-3,4-O-isopropylidene-D-mannitol

Conditions
ConditionsYield
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℃;
trityl chloride
76-83-5

trityl chloride

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

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

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

O3,O4-isopropylidene-O1,O6-ditrityl-D-mannitol

Conditions
ConditionsYield
With dmap In pyridine at 22℃; for 48h;97%
With pyridine for 48h; Ambient temperature;74%
With pyridine at 20℃; for 48h;
pivaloyl chloride
3282-30-2

pivaloyl chloride

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

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

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

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

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 24h;95%
propargyl bromide
106-96-7

propargyl bromide

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

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

C21H26O6

C21H26O6

Conditions
ConditionsYield
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%
1-triphenylphosphoranylidene-2-propanone
1439-36-7

1-triphenylphosphoranylidene-2-propanone

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

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

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

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

Conditions
ConditionsYield
With sodium periodate; silica gel In dichloromethane at 20℃; for 20h; Wittig reaction;92%
benzoyl chloride
98-88-4

benzoyl chloride

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

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

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

1,6-di-O-benzoyl-3,4-di-O-isopropylidene-D-mannitol

Conditions
ConditionsYield
With pyridine In dichloromethane at -80℃; for 4h;90%
With pyridine In chloroform at 0℃;80%
With pyridine In dichloromethane72%
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

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

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

mannitol triacetonide
3969-59-3

mannitol triacetonide

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 48h; Heating;89%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

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

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

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

1,6-di-O-(p-toluenesulfonyl)-3,4-O-isopropylidene-D-mannitol

Conditions
ConditionsYield
With pyridine Tosylation;86%
In pyridine at 0℃; for 3.75h;84%
With pyridine
benzyl bromide
100-39-0

benzyl bromide

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

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

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

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

Conditions
ConditionsYield
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; toluene65%
With di(n-butyl)tin oxide; cesium fluoride 1.) toluene; Yield given. Multistep reaction;
benzyl bromide
100-39-0

benzyl bromide

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

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

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

1,2,5,6-tetra-O-benzyl-D-mannitol

Conditions
ConditionsYield
With hydrogenchloride; acetyl chloride In methanol; hexane; N,N-dimethyl-formamide81%
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
benzyl chloride
100-44-7

benzyl chloride

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

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

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

1,2,5,6-tetra-O-benzyl-3,4-O-isopropylidene-D-mannitol

Conditions
ConditionsYield
With sodium hydroxide; potassium carbonate; tert-Amyl alcohol; tetra(n-butyl)ammonium hydrogensulfate In dimethyl sulfoxide; benzene for 12h; Ambient temperature;80%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

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

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

C37H42O14S4

C37H42O14S4

Conditions
ConditionsYield
With pyridine; triethylamine at 0 - 20℃; for 48h;79%
phenyl isocyanate
103-71-9

phenyl isocyanate

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

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

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

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

Conditions
ConditionsYield
With Zn naphthenate; triethylamine In N,N-dimethyl-formamide for 1h; Ambient temperature;77%
1-Bromotetradecane
112-71-0

1-Bromotetradecane

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

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

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

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

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 25℃; for 48h;76%
4-Fluorobenzyl bromide
459-46-1

4-Fluorobenzyl bromide

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

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

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

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

Conditions
ConditionsYield
73%
4-trifluoromethylbenzyl chloride
939-99-1

4-trifluoromethylbenzyl chloride

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

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

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

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

Conditions
ConditionsYield
72%
3,4-di-O-isopropylidene-D-mannitol
3969-84-4

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

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

1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol

Conditions
ConditionsYield
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
ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

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

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

(E)-3-[(4R,5R)-5-((E)-2-Ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid ethyl ester
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
ConditionsYield
With sodium periodate; silica gel In dichloromethane at 20℃; for 20h; Wittig reaction;67%
4-Methylbenzyl bromide
104-81-4

4-Methylbenzyl bromide

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

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

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

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

Conditions
ConditionsYield
65%
4-cyanobenzyl bromide
17201-43-3

4-cyanobenzyl bromide

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

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

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

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

Conditions
ConditionsYield
65%
trityl chloride
76-83-5

trityl chloride

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

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

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

3,4-O-isopropylidene-1-O-trityl-D-mannitol

Conditions
ConditionsYield
With pyridine Ambient temperature;63%
3,4-di-O-isopropylidene-D-mannitol
3969-84-4

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

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

(2R,3R,4R,5R)-3,4-O-(1-methylethylidene)-2,3,4,5-hexanetetraol

Conditions
ConditionsYield
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
3,4-di-O-isopropylidene-D-mannitol
3969-84-4

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

methyl iodide
74-88-4

methyl iodide

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

3,4-O-isopropylidene-1,2,5,6-tetra-O-methyl-D-mannitol

Conditions
ConditionsYield
With sodium methylsulfinylmethanide In dimethyl sulfoxide 1.) 0 degC, 2.) 0 degC to r.t.;60%
3,4-di-O-isopropylidene-D-mannitol
3969-84-4

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

C18H30O12P2

C18H30O12P2

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

3969-84-4Relevant academic research and scientific papers

A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides

Miller, Gavin J.,Broberg, Karl. R.,Rudd, Claire,Helliwell, Madeleine R.,Jayson, Gordon C.,Gardiner, John M.

, p. 11208 - 11219 (2015/11/27)

d-Glucosamine derivatives bearing latent O4 functionality provide modified H/HS-type disaccharide donors for a final stage capping approach enabling introduction of conjugation-suitable, non-reducing terminal functionality to biologically important glycosaminoglycan oligosaccharides. Application to the synthesis of the first O4-terminus modified synthetic LMWH decasaccharide and an HS-like dodecasaccharide is reported.

Synthesis of N-oxyamide-linked neoglycolipids

Chen, Na,Xie, Juan

, p. 10716 - 10721 (2015/02/19)

N-Oxyamide-containing compounds have shown improved metabolic stability and interesting secondary structures due to the good hydrogen bond-donating property of N-oxyamide. β-Glucolipids linked by the N-oxyamide bond have been successfully synthesized as novel mimics of glycoglycerolipids and glycosphingolipids.

A NOVEL PROCESS FOR MAKING ALISKIREN, ITS NOVEL INTERMEDIATES AND CERTAIN NOVEL COMPOUNDS

-

, (2011/06/23)

A novel process for making Renin inhibitors like Aliskiren is disclosed. Its novel intermediate compounds and method of making them are also disclosed.

Zeolite catalyzed selective deprotection of di- and tri-O-isopropylidene sugar acetals

Bhaskar, Pallooru Muni,Mathiselvam, Manoharan,Loganathan, Duraikkannu

, p. 1801 - 1807 (2008/12/21)

H-Beta zeolite, a microporous solid acid, is demonstrated to be an efficient catalyst for the selective deprotection of cyclic as well as acyclic O-isopropylidene sugar acetals derived from d-glucose, d-xylose, d-mannose, and d-mannitol in aqueous MeOH at room temperature. A notable observation is the conversion of d-mannitol triacetonide into 1,2:3,4-di-O-isopropylidene-d-mannitol (48%) and 3,4-O-isopropylidene-d-mannitol (36%) brought about in 6 h by H-beta zeolite and the non-occurrence of any hydrolysis in the case of H-ZSM-5 catalyzed reaction in 24 h under the same conditions.

Bifunctional acyclic nucleoside phosphonates: synthesis of chiral 9-{3-hydroxy[1,4-bis(phosphonomethoxy)]butan-2-yl} derivatives of purines

Vrbkova, Silvie,Dracinsky, Martin,Holy, Antonin

, p. 2233 - 2247 (2008/02/11)

We report herein a general method for the synthesis of new types of chiral acyclic nucleoside four-carbon bisphosphonates. The alkylation of 2-amino-6-chloropurine and adenine was performed with (2S,3S)- or (2R,3R)-1,4-[bis(diisopropoxyphosphoryl)methoxy]]-3-[(methylsulfonyl)oxy]butan-2-yl benzoate. Alkylations provided (2R,3R) or (2S,3S) N9-substituted nucleobases, which were further converted to other derivatives. These conversions included either a modification of the nucleobase or transformation of the bisphosphonate chain. Subsequent deprotection of the diisopropyl esters with bromotrimethylsilane provided the resulting (2R,3R)- or (2S,3S)-bisphosphonic acids.

An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal

Hanaya, Tadashi,Nakamura, Yuichi,Yamamoto, Hiroshi

, p. 983 - 989 (2008/09/19)

(R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.

Synthesis and DNA-binding ability of pyrrolo[2,1-c][1,4]benzodiazepine- azepane conjugates

Kamal, Ahmed,Reddy, D. Rajasekhar,Reddy, P. S. Murali Mohan,Rajendar

, p. 1160 - 1163 (2007/10/03)

A series of pyrrolobenzodiazepine-azepane conjugates linked through different alkane spacers have been prepared and their DNA thermal denaturation studies have been carried out. One of the compound (4b), elevates the DNA helix melting temperature of the CT-DNA by 2.0°C after incubation for 36 h at 37°C.

Asymmetric catalysis based on chiral phospholanes and hydroxyl phospholanes

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Page column 14-15, (2010/02/06)

Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.

A Novel Chiral Ferrocenyl Phosphine Ligand from Sugar: Applications in Rh-Catalyzed Asymmetric Hydrogenation Reactions

Liu, Duan,Li, Wenge,Zhang, Xumu

, p. 4471 - 4474 (2007/10/03)

(Matrix Presented) A new chiral ferrocenyl diphosphine ligand 3 was synthesized from readily available D-mannitol. Rh-complex with this ligand showed high enantioselectivity and reactivity in the asymmetric hydrogenation of dehydroamino acid derivatives and itaconic acid derivatives. Up to over 99% ee and 10 000 TON were achieved with this catalytic system.

Asymmetric catalysis based on chiral phospholanes and hydroxyl phospholanes

-

Page column 14-15, (2010/01/30)

Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.

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