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Benzaldehyde dimethyl acetal CAS NO.1125-88-8
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Benzaldehyde dimethyl acetal
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Benzaldehyde dimethyl acetal / LIDE PHARMA- Factory supply / Best price
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1125-88-8 Usage

Chemical Properties

Clear colorless liquid

Chemical Properties

Benzaldehyde dimethyl acetal has a sweet, floral note; also reminiscent of almond

Occurrence

Reported found in rhubarb and potato.

Uses

Benzaldehyde dimethyl acetal used as an effective reagent for the construction of selenocarbonyl compounds.

Uses

Benzaldehyde dimethyl acetal is suitable for use in the synthesis of 4,6-dihydroxy sugar, required for the total synthesis of Porphyromonas gingivalis 381 derived lipid A. It may be used in the preparation of 1-O-methyl-2,3-di-O-galloyl-β-D-glucose.

Uses

Benzaldehyde dimethyl acetal may be used as an analytical reference standard for the quantification of the analyte in fresh and canned fish and Cinnamomum zeylanicum using gas-chromatography coupled to mass spectrometry (GC-MS).

Preparation

From benzaldehyde and methanol in the presence of calcium chloride and HCl; from benzaldehyde and tetramethylorthosilicate in the presence of anhydrous HCl in methanol

Preparation

A mixture of ethylenediamine (1.2 g, 20 mmol), Ph3SbO (1.0 mmol), and P4S10 (2.0 mmol) was autoclaved under a pressure of CO2 (4.9 MPa). Imidazolidinone was isolated by column chromatography (silica gel; eluent: ethyl acetate/hexane, 1:1, v/v); yield 1.5 g (85%).

Taste threshold values

Taste characteristics at 25 ppm: green, nutty, brown and sweet

General Description

The abstraction of α-hydrogen atoms from benzaldehyde dimethyl acetal by active bromine at 80°C has been investigated.

Safety Profile

Moderately toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
InChI:InChI=1/C9H12O2/c1-10-9(11-2)8-6-4-3-5-7-8/h3-7,9H,1-2H3

1125-88-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (B1197)  Benzaldehyde Dimethyl Acetal  >98.0%(GC) 1125-88-8 25mL 140.00CNY Detail
TCI America (B1197)  Benzaldehyde Dimethyl Acetal  >98.0%(GC) 1125-88-8 100mL 430.00CNY Detail
TCI America (B1197)  Benzaldehyde Dimethyl Acetal  >98.0%(GC) 1125-88-8 500mL 1,230.00CNY Detail
Alfa Aesar (A11009)  Benzaldehyde dimethyl acetal, 99%    1125-88-8 100g 421.0CNY Detail
Alfa Aesar (A11009)  Benzaldehyde dimethyl acetal, 99%    1125-88-8 500g 1532.0CNY Detail
Alfa Aesar (A11009)  Benzaldehyde dimethyl acetal, 99%    1125-88-8 2500g 6513.0CNY Detail
Aldrich (226076)  Benzaldehydedimethylacetal  99% 1125-88-8 226076-100G 452.79CNY Detail
Aldrich (226076)  Benzaldehydedimethylacetal  99% 1125-88-8 226076-500G 1,751.49CNY Detail
Aldrich (381438)  Benzaldehydedimethylacetal  95% 1125-88-8 381438-100ML 468.00CNY Detail

1125-88-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzaldehyde dimethyl acetal

1.2 Other means of identification

Product number -
Other names α,α-Dimethoxytoluene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1125-88-8 SDS

1125-88-8Synthetic route

benzaldehyde
100-52-7

benzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With [Sc2(C4O4)3]n In tetrachloromethane at 60℃; for 1h;100%
With lithium tetrafluoroborate In methanol for 0.5h; Heating;100%
indium(III) triflate In dichloromethane at 20℃; for 0.0833333h;99%
methanol
67-56-1

methanol

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With trimethyl orthoformate at 20℃; for 0.5h;99%
With cobalt(II) 2-propyliminomethyl-phenolate functionalized mesoporous silica for 2h; Reflux;99%
With Zr6(µ3-O)4(µ3-OH)4(2,2-bis(trifluoromethyl)-4,4’-biphenyldicarboxylate)4[Cu(2,2'-bipyridine-5,5’-dicarboxylate)(MeCN)I](C6H3(NH-CO-C6H4-SO3H)(PhCOO)2) at 20℃; for 2h; Catalytic behavior; Reagent/catalyst;99%
methanol
67-56-1

methanol

3,3,5-triphenyl-1,2,4-trioxolane
23246-12-0

3,3,5-triphenyl-1,2,4-trioxolane

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzophenone
119-61-9

benzophenone

C

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With chlorosulfonic acid for 80h;A 75%
B 95%
C 25%
3,3,5-triphenyl-1,2,4-trioxolane
23246-12-0

3,3,5-triphenyl-1,2,4-trioxolane

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzophenone
119-61-9

benzophenone

C

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With chlorosulfonic acid In methanol for 80h;A 75%
B 95%
C 25%
methanol
67-56-1

methanol

toluene
108-88-3

toluene

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With sodium perchlorate; Tris(2,4-dibromophenyl)amine In dichloromethane indirect electrochemical oxidation; Yields of byproduct given;A 95%
B n/a
C n/a
With lithium perchlorate direct electrochemical oxidation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
methanol
67-56-1

methanol

3-chloro-3-phenyl-3H-diazirine
4460-46-2

3-chloro-3-phenyl-3H-diazirine

A

benzylidene dichloride
98-87-3

benzylidene dichloride

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
at 80℃; for 6h; Mechanism; other 3-chloro-3-aryldiazirines;A n/a
B 95%
C 1%
at 80℃; for 6h;A n/a
B 95%
C 1%
Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h; Product distribution;94%
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h;94%
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h;94%
In dichloromethane at -78℃; for 0.0833333h;
styrene
292638-84-7

styrene

methanol
67-56-1

methanol

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With 2-Picolinic acid; ferrous(II) sulfate heptahydrate; dihydrogen peroxide at 20 - 60℃; for 12h; Schlenk technique; Molecular sieve;93%
With potassium trifluoroacetate at 55 - 60℃; electrochemical oxidation;42 % Spectr.
With tert.-butylhydroperoxide; C30H29ClN4ORu(2+)*2F6P(1-) at 50℃; Catalytic behavior; Kinetics; Reagent/catalyst; Schlenk technique; Molecular sieve;87 %Chromat.
With zinc indium sulfide; phenylmethanethiol for 15h; Irradiation;81 %Chromat.
methanol
67-56-1

methanol

1-propenylbenzene
873-66-5

1-propenylbenzene

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With 2-Picolinic acid; ferrous(II) sulfate heptahydrate; dihydrogen peroxide at 20 - 60℃; for 12h; Schlenk technique; Molecular sieve;93%
methanol
67-56-1

methanol

2-phenyl-1,3-oxathiolane
5721-88-0

2-phenyl-1,3-oxathiolane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With N-Bromosuccinimide at 20℃; for 0.166667h;92%
methanol
67-56-1

methanol

benzaldehyde
100-52-7

benzaldehyde

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With oxygen; Pd5-Bi2-Pb1-Fe1/(100)SiO2-MgOA 90.3%
B n/a
With oxygen; Pd5-Bi2-Fe1/(100)SiO2-MgOA 88.8%
B n/a
With oxygen; Pd5-Bi2-Pb1-Co1/(100)SiO2A 88.6%
B n/a
methanol
67-56-1

methanol

3-α-bromobenzyloxy-3-fluorodiazirine
138173-30-5

3-α-bromobenzyloxy-3-fluorodiazirine

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism; also in the presence of HCl or bases, use of CD3OD/CD3CN, also with ethylene glycol or piperidine;90%
methanol
67-56-1

methanol

[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

benzaldehyde benzylidenehydrazone
28867-76-7

benzaldehyde benzylidenehydrazone

A

iodobenzene
591-50-4

iodobenzene

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With sodium methylate at 0 - 25℃; for 48h; Product distribution; Var. aldazines and alcohols;A n/a
B 88%
methanol
67-56-1

methanol

benzaldehyde benzylidenehydrazone
28867-76-7

benzaldehyde benzylidenehydrazone

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; sodium methylate at 0 - 25℃; for 48h;88%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
trimethylsilyl iodide In dichloromethane 1.) -78 deg C, 3 h, 2.) RT, 4h;87%
With hydrogenchloride
methanol
67-56-1

methanol

N-Benzylidenemethylamine
622-29-7

N-Benzylidenemethylamine

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With bromine for 1h; Heating;87%
methanol
67-56-1

methanol

2-phenyl-1,3-dithiane
5616-55-7

2-phenyl-1,3-dithiane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With N-Bromosuccinimide at 20℃; for 0.0833333h;86%
trifluoroacetic acid-methyl ester
431-47-0

trifluoroacetic acid-methyl ester

sodium methylate
124-41-4

sodium methylate

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
In methanol at 20℃; Inert atmosphere;85%
methanol
67-56-1

methanol

chalcone epoxide
5411-12-1

chalcone epoxide

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

C

2-hydroxy-3-methoxy-1,3-diphenylpropan-1-one
412017-63-1

2-hydroxy-3-methoxy-1,3-diphenylpropan-1-one

Conditions
ConditionsYield
With tetraethylammonium bromide at 25℃; Product distribution; reaction in CH3OD and nitromethane (1:50); in acetic acid; retention/inversion products;A 2%
B 13%
C 84%
benzaldehyde
100-52-7

benzaldehyde

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

2,2-dimethoxy-propane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 70℃; Addition;84%
With toluene-4-sulfonic acid67%
methanol
67-56-1

methanol

1,2-dimethoxyethylbenzene
32345-80-5, 4013-37-0

1,2-dimethoxyethylbenzene

A

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

B

1-phenyl-1,1,2-trimethoxyethane
143191-51-9

1-phenyl-1,1,2-trimethoxyethane

Conditions
ConditionsYield
With potassium fluoride; 100 mA cm-2 at 60℃; Product distribution; various supporting electrolytes and anode materials;A 82%
B 10%
With potassium fluoride at 60℃; 100 mA cm-2, Pt anode;A 82%
B 10%
styrene
292638-84-7

styrene

methanol
67-56-1

methanol

A

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

B

1,2-dimethoxyethylbenzene
32345-80-5, 4013-37-0

1,2-dimethoxyethylbenzene

C

1,4-dimethoxy-1,4-diphenylbutane
32673-77-1

1,4-dimethoxy-1,4-diphenylbutane

D

1-phenyl-1,2,2-trimethoxy ethane
54845-42-0

1-phenyl-1,2,2-trimethoxy ethane

Conditions
ConditionsYield
With potassium fluoride at 60℃; 100 mA cm-2, Pt anode; Further byproducts given;A 1%
B 80%
C 3%
D 5%
With TPC at 60℃; 100 mA cm-2, C anode;A 16%
B 45%
C 13%
D 2%
styrene
292638-84-7

styrene

methanol
67-56-1

methanol

A

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

B

1,2-dimethoxyethylbenzene
32345-80-5, 4013-37-0

1,2-dimethoxyethylbenzene

C

1,4-dimethoxy-1,4-diphenylbutane
32673-77-1

1,4-dimethoxy-1,4-diphenylbutane

D

1-phenyl-1,2,2-trimethoxy ethane
54845-42-0

1-phenyl-1,2,2-trimethoxy ethane

E

meso-1,4-dimethoxy-2,3-diphenylbutane
80621-69-8

meso-1,4-dimethoxy-2,3-diphenylbutane

F

1,4-dimethoxy-1,3-diphenylbutane
80634-49-7

1,4-dimethoxy-1,3-diphenylbutane

Conditions
ConditionsYield
With potassium fluoride; 100 mA cm-2 at 60℃; Product distribution; various supporting electrolytes and anode materials;A 1%
B 80%
C 3%
D 5%
E 2%
F 2%
methanol
67-56-1

methanol

benzaldehyde
100-52-7

benzaldehyde

acetophenone
98-86-2

acetophenone

A

acetophenone dimethyl acetal
4316-35-2

acetophenone dimethyl acetal

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With CoCl2 for 2h; Heating;A n/a
B 77%
benzylidene dichloride
98-87-3

benzylidene dichloride

trimethyl orthoformate
149-73-5

trimethyl orthoformate

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
at 225℃; for 39h;76%
With zinc(II) chloride at 20 - 25℃; for 1h;
methanol
67-56-1

methanol

benzaldehyde
100-52-7

benzaldehyde

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With Eco1a; dihydrogen peroxide In water at 20℃; for 17h; Reflux;A 76%
B 10%
C 11%
With dihydrogen peroxide; zinc(II) chloride In water at 20℃;
With oxygen at 179.84℃; under 7500.75 Torr; for 2h; Inert atmosphere;
styrene
292638-84-7

styrene

methanol
67-56-1

methanol

A

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With tert.-butylhydroperoxide; C29H25Cl2N4Ru(1+)*F6P(1-) at 50℃; for 6h; Reagent/catalyst; Schlenk technique; Molecular sieve;A 73%
B 7%
With ozone; thiourea 1) -10-(-15) deg C, 65 min, CH3OH; 2) 0 deg C, 55 min; Yield given. Multistep reaction;
α-chlorobenzyl methyl ether
35364-99-9

α-chlorobenzyl methyl ether

trimethyl orthoformate
149-73-5

trimethyl orthoformate

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
at 20℃; for 24h;72%
α-chlorobenzyl methyl ether
35364-99-9

α-chlorobenzyl methyl ether

trimethyl orthoformate
149-73-5

trimethyl orthoformate

A

Methyl formate
107-31-3

Methyl formate

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
A n/a
B 72%
methanol
67-56-1

methanol

Cyclohepta-1,3,5-triene
544-25-2

Cyclohepta-1,3,5-triene

A

7-methoxy-1,3,5-cycloheptatriene
1714-38-1

7-methoxy-1,3,5-cycloheptatriene

B

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With sodium methylate; tetraethylammonium tosylate at -10 - 0℃; anodic oxidation;A 71%
B 15%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

4-methoxy-4-phenyl-1-butene
22039-97-0

4-methoxy-4-phenyl-1-butene

Conditions
ConditionsYield
With trimethylaluminum; aluminum tri-bromide; copper(I) bromide In dichloromethane; toluene at 20℃; for 3h;100%
With 2,4-dinitrobenzenesulfonic acid In acetonitrile at 20℃; for 1h; Hosomi-Sakurai reaction;99%
With 30% bis[triphenyl(3-sulfopropyl)phosphonium]HPW12O40/SiO2 In acetonitrile at 20℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Solvent; Hosomi-Sakurai Reaction; Inert atmosphere; Green chemistry; chemoselective reaction;99%
4-methoxy-5H-furan-2-one
69556-70-3

4-methoxy-5H-furan-2-one

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

methyl 5-(1-methoxybenzyl)tetronate
82204-21-5

methyl 5-(1-methoxybenzyl)tetronate

Conditions
ConditionsYield
zinc dibromide100%
With n-butyllithium; boron trifluoride diethyl etherate 1.) ether, hexane, -78 deg C, 2.) ether, -78 deg C.; Yield given. Multistep reaction;
1-styrenyloxytrimethylsilane
13735-81-4

1-styrenyloxytrimethylsilane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

3-methoxy-1,3-diphenylpropan-1-one
89524-37-8

3-methoxy-1,3-diphenylpropan-1-one

Conditions
ConditionsYield
polymeric dicyanoketene acetal In acetonitrile for 6.5h; Substitution; Heating;100%
With polymer-supported DCKA In acetonitrile for 6.5h; Heating;100%
With Celite; polystyrene-bound super Broensted acid In toluene at 20℃; flow system;99%
1-styrenyloxytrimethylsilane
13735-81-4

1-styrenyloxytrimethylsilane

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

1,3-diphenyl-propen-3-one
614-47-1

1,3-diphenyl-propen-3-one

Conditions
ConditionsYield
With chloromethyl methyl ether; tin(ll) chloride In dichloromethane for 2h; Ambient temperature;100%
1-(Trimethylsilyloxy)cyclohexene
6651-36-1

1-(Trimethylsilyloxy)cyclohexene

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(E)-2-benzylidenecyclohexanone
5682-83-7, 31021-02-0, 1467-15-8

(E)-2-benzylidenecyclohexanone

Conditions
ConditionsYield
With acetyl chloride; tin(ll) chloride In dichloromethane for 2h; Product distribution; Ambient temperature; effect of catalyst-activator system;100%
With acetyl chloride; tin(ll) chloride In dichloromethane for 2h; Ambient temperature;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

tributyltin phenyl sulfide
17314-33-9

tributyltin phenyl sulfide

(methoxy(phenylthio))methylbenzene
13865-07-1

(methoxy(phenylthio))methylbenzene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In hexane; toluene addn. of BF3*OEt2 in toluene to the acetal in toluene at -78°C and stirring for 1 h; GLC analysis;100%
With boron trifluoride diethyl etherate In hexane; toluene at -78℃; for 1h;100 % Chromat.
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

2-methoxy-2-phenylacetonitrile
13031-13-5

2-methoxy-2-phenylacetonitrile

Conditions
ConditionsYield
With titanium tetrachloride at -78 - -30℃;100%
With titanium tetrachloride In dichloromethane at -70 - 20℃; for 3h;96%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In water at 30℃; for 0.0833333h;100%
With water at 80℃; for 2h;100%
With water at 90℃; Inert atmosphere;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol
2936-70-1, 5624-48-6, 13992-15-9, 16758-34-2, 28244-97-5, 77481-62-0, 77481-63-1, 105088-17-3, 149495-84-1

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
71676-30-7, 87508-18-7, 138922-03-9, 87508-17-6

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 60℃; pH=2 - 3; Inert atmosphere;100%
With 1,3,5-trichloro-2,4,6-triazine In acetonitrile at 60℃; for 0.166667h; Sonication; Inert atmosphere; regioselective reaction;95%
With iron(III) chloride In acetonitrile at 20℃; for 2.5h; regioselective reaction;92%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

5,5-dimethyl-2-phenyl-[1,3]dioxane
776-88-5

5,5-dimethyl-2-phenyl-[1,3]dioxane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane Inert atmosphere;100%
With 4 A molecular sieve; camphor-10-sulfonic acid In dichloromethane for 0.5h;99%
With camphor-10-sulfonic acid In dichloromethane Ambient temperature;97%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,4R,5R)-5-Methyl-hept-6-ene-2,4-diol
163380-63-0

(2R,4R,5R)-5-Methyl-hept-6-ene-2,4-diol

(4R,6R)-4-Methyl-6-((R)-1-methyl-allyl)-2-phenyl-[1,3]dioxane

(4R,6R)-4-Methyl-6-((R)-1-methyl-allyl)-2-phenyl-[1,3]dioxane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane at 25℃; for 1.5h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,4S,5S)-5-Methyl-hept-6-ene-2,4-diol
155581-30-9

(2R,4S,5S)-5-Methyl-hept-6-ene-2,4-diol

(4R,6S)-4-Methyl-6-((S)-1-methyl-allyl)-2-phenyl-[1,3]dioxane

(4R,6S)-4-Methyl-6-((S)-1-methyl-allyl)-2-phenyl-[1,3]dioxane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In dichloromethane at 25℃; for 1.5h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(Z)-(1R,4S,7R,8R)-3-Allyl-4,8-bis-benzyloxy-7-methoxymethoxy-2,2-dimethyl-cyclooct-5-ene-1,3-diol

(Z)-(1R,4S,7R,8R)-3-Allyl-4,8-bis-benzyloxy-7-methoxymethoxy-2,2-dimethyl-cyclooct-5-ene-1,3-diol

(Z)-(1S,2S,5R,6S,7R,9S)-1-Allyl-2,6-bis-benzyloxy-5-methoxymethoxy-11,11-dimethyl-9-phenyl-8,10-dioxa-bicyclo[5.3.1]undec-3-ene

(Z)-(1S,2S,5R,6S,7R,9S)-1-Allyl-2,6-bis-benzyloxy-5-methoxymethoxy-11,11-dimethyl-9-phenyl-8,10-dioxa-bicyclo[5.3.1]undec-3-ene

Conditions
ConditionsYield
With camphor-10-sulfonic acid In benzene100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

methyl beta-D-glucopyranoside
709-50-2

methyl beta-D-glucopyranoside

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
71117-37-8

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; under 37.5038 Torr; for 2h;100%
With (1S)-10-camphorsulfonic acid In acetonitrile at 20℃; for 4h;93%
With iodine In acetonitrile at 20℃; for 1h;92%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

methyl α-D-galactopyranoside
3396-99-4

methyl α-D-galactopyranoside

methyl 4,6-O-benzylidene-α-D-galactopyranoside
64552-06-3

methyl 4,6-O-benzylidene-α-D-galactopyranoside

Conditions
ConditionsYield
With camphor-10-sulfonic acid In chloroform at 65℃;100%
With tetrafluoroboric acid In diethyl ether; N,N-dimethyl-formamide at 20℃; for 16h;96%
With toluene-4-sulfonic acid; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 2h;92%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester
182865-98-1

((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester

((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester
182865-71-0

((2R,4aR,6R,7R,8R,8aS)-6-Ethoxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid allyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile100%
methanol
67-56-1

methanol

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

Conditions
ConditionsYield
With carbon tetrabromide; oxygen for 5h; Irradiation;100%
With hydrogenchloride; dihydrogen peroxide95%
With dihydrogen peroxide In water at 30℃; for 3h; Green chemistry;65%
With oxygen at 90℃; under 3800.26 Torr; for 2h;
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

tetraallyl tin
7393-43-3

tetraallyl tin

1-Phenyl-3-buten-1-ol
80735-94-0

1-Phenyl-3-buten-1-ol

Conditions
ConditionsYield
With trifluoroacetic acid In ethanol at 30℃; for 20h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(Z)-1-Trimethylsilanyl-5-trimethylsilanyloxy-pent-2-ene
193829-28-6

(Z)-1-Trimethylsilanyl-5-trimethylsilanyloxy-pent-2-ene

(2R,3R)-2-Phenyl-3-vinyl-tetrahydro-furan

(2R,3R)-2-Phenyl-3-vinyl-tetrahydro-furan

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -20℃; for 0.333333h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

Conditions
ConditionsYield
With camphor-10-sulfonic acid In acetonitrile at 20℃; for 12h;100%
With camphor-10-sulfonic acid In acetonitrile at 20℃; regioselective reaction;93%
With toluene-4-sulfonic acid In acetonitrile for 2h; Ambient temperature; Yield given;
With camphor-10-sulfonic acid In acetonitrile at 20℃;
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,3S,4R)-3-Benzyloxy-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-1,1-bis-ethylsulfanyl-pentane-2,4-diol
199850-99-2

(2R,3S,4R)-3-Benzyloxy-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-1,1-bis-ethylsulfanyl-pentane-2,4-diol

{4-[(2R,4R,5S,6R)-5-Benzyloxy-6-(bis-ethylsulfanyl-methyl)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2,6-dimethoxy-phenoxy}-tert-butyl-dimethyl-silane

{4-[(2R,4R,5S,6R)-5-Benzyloxy-6-(bis-ethylsulfanyl-methyl)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2,6-dimethoxy-phenoxy}-tert-butyl-dimethyl-silane

Conditions
ConditionsYield
With camphor-10-sulfonic acid In benzene for 0.333333h; Ambient temperature;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

(2R,3R,4S,5S,6R)-2-Dicyclohexylmethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
197164-63-9

(2R,3R,4S,5S,6R)-2-Dicyclohexylmethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

(2R,4aR,6R,7R,8R,8aS)-6-Dicyclohexylmethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
197164-99-1

(2R,4aR,6R,7R,8R,8aS)-6-Dicyclohexylmethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Conditions
ConditionsYield
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 57℃; under 20 Torr; for 3h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

N-(2-hydroxycyclohexyl)-4-methylbenzenesulfonamide
58107-40-7, 69291-83-4

N-(2-hydroxycyclohexyl)-4-methylbenzenesulfonamide

(3aR,7aS)-2-Phenyl-3-(toluene-4-sulfonyl)-octahydro-benzooxazole

(3aR,7aS)-2-Phenyl-3-(toluene-4-sulfonyl)-octahydro-benzooxazole

Conditions
ConditionsYield
With 4 A molecular sieve; pyridinium p-toluenesulfonate In toluene for 48h; Heating;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

trans-2-(tert-butylamino)cyclohexan-1-ol
55915-78-1, 65760-72-7, 109735-34-4, 131164-09-5

trans-2-(tert-butylamino)cyclohexan-1-ol

(3a,7a-trans)-octahydro-3-(t-butyl)-2-phenylbenzoxazole

(3a,7a-trans)-octahydro-3-(t-butyl)-2-phenylbenzoxazole

Conditions
ConditionsYield
With 4 Angstroem molecular sives; pyridinium p-toluenesulfonate In toluene for 100h; Heating;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

phenyl-β-D-glucopyranoside
1464-44-4

phenyl-β-D-glucopyranoside

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 12h;100%
With sodium hydrogen sulfate; silica gel In acetonitrile at 20℃; for 4h;95%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 0℃; for 48h;95%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

acetophenone
98-86-2

acetophenone

tributyl-(1-ethoxy-vinyloxy)-silane

tributyl-(1-ethoxy-vinyloxy)-silane

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

A

4-methoxy-4-phenyl-1-butene
22039-97-0

4-methoxy-4-phenyl-1-butene

B

3-phenyl-3-tributylsilanyloxy-butyric acid ethyl ester

3-phenyl-3-tributylsilanyloxy-butyric acid ethyl ester

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 9h; parallel recognition;A 100%
B 95%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate
220384-85-0

ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate
220384-86-1

ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate

Conditions
ConditionsYield
With camphor-10-sulfonic acid In benzene for 1h; Heating;100%
With camphor-10-sulfonic acid In benzene for 1h; Cyclization; Heating;95%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine
316804-46-3

6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

6-O-(4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine
316804-47-4

6-O-(4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 60℃; under 35 Torr; for 1h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate
212136-31-7

ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate

(2S,4R,5R)-5-Methyl-5-methylsulfanyl-2,4-diphenyl-[1,3]dioxane

(2S,4R,5R)-5-Methyl-5-methylsulfanyl-2,4-diphenyl-[1,3]dioxane

Conditions
ConditionsYield
Stage #1: ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate With lithium borohydride In dichloromethane at 20℃;
Stage #2: benzaldehyde dimethyl acetal With camphor-10-sulfonic acid In dichloromethane at 20℃;
100%
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