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453-17-8 Usage

Description

D-(+)-Glyceraldehyde is an intermediate in carbohydrate metabolism. It is phosphorylated by triose kinase to produce D-glyceraldehyde 3-phosphate, an intermediate in glycolysis, gluconeogenesis, photosynthesis, and other metabolic pathways.

Chemical Properties

CLEAR ORANGE SYRUP

Uses

Different sources of media describe the Uses of 453-17-8 differently. You can refer to the following data:
1. D-Glyceraldehyde is the simplest of all aldoses and have been shown to be the one of the carbonyl metabolite of dietary fructose.
2. D-(+)-Glyceraldehyde can be utilized as a reactant in the synthesis of: (S)-homophenylalanine by ruthenium oxidation of a 3-amino-1,2-diol generated via coupling of an amine, and α-hydroxyaldehyde.β- and γ-allenols via metal-catalyzed cyclization. Allenols are used as a key precursor for the preparation of enantiopure dihydropyrans and tetrahydrooxepines.Isopropylidene D-glyceraldehyde intermediate, which controls the chirality in the total synthesis of prostaglandins (PGE1).

Definition

ChEBI: The D-enantiomer of glyceraldehyde.

Purification Methods

enantiomer [453-17-8] is a syrup (70 + % H2O) with [] D +14o (c 2, H2O) and the dimethyl acetal has b 124-127 o/14mm and []15 +21o (c 18, H2O). [Beilstein 1 H 845, 1 IV 4114.]

Check Digit Verification of cas no

The CAS Registry Mumber 453-17-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,5 and 3 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 453-17:
(5*4)+(4*5)+(3*3)+(2*1)+(1*7)=58
58 % 10 = 8
So 453-17-8 is a valid CAS Registry Number.
InChI:InChI=1/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2/t3-/m0/s1

453-17-8 Well-known Company Product Price

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  • Aldrich

  • (49800)  D-(+)-Glyceraldehyde  ≥98.0% (HPLC), viscous

  • 453-17-8

  • 49800-1G

  • 1,958.58CNY

  • Detail
  • Aldrich

  • (49800)  D-(+)-Glyceraldehyde  ≥98.0% (HPLC), viscous

  • 453-17-8

  • 49800-5G

  • 7,844.85CNY

  • Detail

453-17-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (2R)-2,3-dihydroxypropanal

1.2 Other means of identification

Product number -
Other names Propanal, 2,3-dihydroxy-, (R)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:453-17-8 SDS

453-17-8Synthetic route

Conditions
ConditionsYield
With E. coli BL21 (DE3) cells harboring pETDRhaD aldolase; sodium borate buffer In water; toluene at 37℃; for 16h; pH=7.6;A n/a
B 92%
D-glyceraldehyde-3-phosphate
591-57-1

D-glyceraldehyde-3-phosphate

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With Potato acid phosphatase (Pase) In water85%
D-Fructose
57-48-7

D-Fructose

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid Erwaermen des Reaktionsprodukts mit wss.Schwefelsaeure;
(R)-3,3-dimethoxy-propane-1,2-diol
18376-33-5

(R)-3,3-dimethoxy-propane-1,2-diol

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Glyceraldehyde
56-82-6

Glyceraldehyde

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With bacterium coli
With bacterium lactis aerogenes
D-Fructose
57-48-7

D-Fructose

A

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

B

D-erythrose
583-50-6

D-erythrose

Conditions
ConditionsYield
With iron(III) chloride In water at 20℃; for 2h; Product distribution; Kinetics; Mechanism; Irradiation; anaerobic and aerobic conditions; other reagent: Fe(NO3)3; various reaction times.;
D-ribose
50-69-1

D-ribose

A

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

B

D-erythrose
583-50-6

D-erythrose

Conditions
ConditionsYield
With iron(III) chloride In water at 20℃; for 3h; Product distribution; Irradiation;
D-glucose
50-99-7

D-glucose

A

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

B

D-Arabinose
10323-20-3

D-Arabinose

C

D-erythrose
583-50-6

D-erythrose

Conditions
ConditionsYield
With iron(III) chloride In water at 20℃; for 3h; Product distribution; Kinetics; Mechanism; Irradiation; various reaction times.;
dihydroxyacetone
96-26-4

dihydroxyacetone

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With trisodium arsenate; triosephosphate isomerase
With 1H-imidazole; xylose isomerase; sodium chloride; magnesium chloride In water at 25℃; pH=8; pH-value; Enzymatic reaction;
(R)-3,3-diethoxypropane-1,2-diol
114882-91-6

(R)-3,3-diethoxypropane-1,2-diol

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With sulfuric acid at 35℃; for 20h;
(6R,7R,14R)-14-formyl-1,8,13,16-tetraoxodispiro<5.0.5.4>-hexadecane
141650-88-6

(6R,7R,14R)-14-formyl-1,8,13,16-tetraoxodispiro<5.0.5.4>-hexadecane

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With trifluoroacetic acid for 1h; Ambient temperature;
3-[(1R)-1,2-dihydroxyethyl]-1,5-dihydro-3H-2,4-benzodioxepine
153323-30-9

3-[(1R)-1,2-dihydroxyethyl]-1,5-dihydro-3H-2,4-benzodioxepine

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In methanol at 25℃; under 2585.7 Torr; for 48h;
2,3-isopropylidene-glyceraldehyde
15186-48-8

2,3-isopropylidene-glyceraldehyde

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With sulfuric acid In water at 45℃; for 1.5h;
With sulfuric acid
With DOWEX 50 W (H+) In tetrahydrofuran; water at 20℃; Inert atmosphere;
Glyceraldehyde
56-82-6

Glyceraldehyde

bacterium coli

bacterium coli

yeast water

yeast water

calcium dicarbonate

calcium dicarbonate

A

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

B

(S)-glyceraldehyde
497-09-6

(S)-glyceraldehyde

Conditions
ConditionsYield
at 37℃;
Glyceraldehyde
56-82-6

Glyceraldehyde

bacterium lactis aerogenes

bacterium lactis aerogenes

yeast water

yeast water

calcium dicarbonate

calcium dicarbonate

A

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

B

(S)-glyceraldehyde
497-09-6

(S)-glyceraldehyde

Conditions
ConditionsYield
at 37℃;
1.2;5.6-diisopropylidene-D-mannitol

1.2;5.6-diisopropylidene-D-mannitol

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With lead(IV) acetate; benzene und Verseifung mit verd. H2SO4 oder Essigsaeure;
With lead(IV) acetate; acetic acid und Verseifung mit verd. H2SO4 oder Essigsaeure;
mannitol
69-65-8

mannitol

water
7732-18-5

water

sodium periodate

sodium periodate

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
at 20℃;
mannitol
69-65-8

mannitol

water
7732-18-5

water

periodic acid

periodic acid

A

formaldehyd
50-00-0

formaldehyd

B

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

C

D-Arabinose
10323-20-3

D-Arabinose

D

Glycolaldehyde
141-46-8

Glycolaldehyde

Conditions
ConditionsYield
at 0℃; weitere Produkt: Ameisensaeure;
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

water
7732-18-5

water

A

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

C

D-Arabinose
10323-20-3

D-Arabinose

D

D-fructosazine

D-fructosazine

Conditions
ConditionsYield
Produkt 5: Melanoidin;
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

aqueous sodium phosphate

aqueous sodium phosphate

A

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

C

D-Arabinose
10323-20-3

D-Arabinose

D

D-fructosazine

D-fructosazine

Conditions
ConditionsYield
Produkt 5: Melanoidin;
D-glyceraldehyde, hydrated form
91987-77-8

D-glyceraldehyde, hydrated form

A

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

B

water

water

Conditions
ConditionsYield
In water at 20 - 80℃; Equilibrium constant; Thermodynamic data; From measured specific rotation of the equilibrium mixture of D-glyceraldehyde and its hydrate and equilibrium constant calculated specific rotation of both compounds at 436, 546 and 589 nm.;
2-Deoxy-D-ribose
533-67-5

2-Deoxy-D-ribose

A

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; D-deoxyribose-5-phosphate aldolase; triethanolamine hydrochloride In water at 25℃; pH=7.5; Kinetics; Further Variations:; Reagents;
dihydroxyacetone phosphate
57-04-5

dihydroxyacetone phosphate

Glyceraldehyde
56-82-6

Glyceraldehyde

A

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

B

L-fructose 1-phosphate
19456-80-5

L-fructose 1-phosphate

Conditions
ConditionsYield
With sodium hydroxide; rhamnulose-1-phosphate aldolase; zinc(II) chloride; potassium phosphate buffer In water at 23℃; for 48h; pH=6.8;
formaldehyd
50-00-0

formaldehyd

Glycolaldehyde
141-46-8

Glycolaldehyde

A

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

B

(S)-glyceraldehyde
497-09-6

(S)-glyceraldehyde

Conditions
ConditionsYield
With L-proline optical yield given as %ee;
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

1,1-Diphenylhydrazine
530-50-7

1,1-Diphenylhydrazine

C15H16N2O2

C15H16N2O2

Conditions
ConditionsYield
With acetic acid In methanol for 1h;95%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

1,1-dihydroxyacetone
1186-47-6

1,1-dihydroxyacetone

D-fructose

D-fructose

Conditions
ConditionsYield
With transaldolase B F178Y/R181E In water-d2 at 25℃; for 24h; Kinetics; Reagent/catalyst; Aldol reaction; Enzymatic reaction; stereoselective reaction;94%
With his6-transaldolase B F178Y/R181E Kinetics; Reagent/catalyst; Aldol reaction; Enzymatic reaction;
fur-2-ylboronic acid
13331-23-2

fur-2-ylboronic acid

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

4-methoxybenzoic acid hydrazide
3290-99-1

4-methoxybenzoic acid hydrazide

C15H18N2O5

C15H18N2O5

Conditions
ConditionsYield
In methanol at 25℃; for 24h; Petasis Reaction; diastereoselective reaction;94%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

dopamine hydrochloride
62-31-7

dopamine hydrochloride

(1'S)-1-(1',2'-dihydroxyethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline
259183-94-3

(1'S)-1-(1',2'-dihydroxyethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
In methanol Heating;93%
In methanol 1) RT, overnight, 2) reflux, 2 d;93%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

Conditions
ConditionsYield
With sodium anthraquinone-2-sulfonate; calcium chloride In sodium hydroxide at 50℃;92%
With water; bromine
With bromine; silver carbonate
With bromine In water for 2h;
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

acetylacetone
123-54-6

acetylacetone

1-(5-(hydroxymethyl)-2-methylfuran-3-yl)ethan-1-one
70107-20-9

1-(5-(hydroxymethyl)-2-methylfuran-3-yl)ethan-1-one

Conditions
ConditionsYield
With zirconium(IV) chloride In water-d2 at 20℃; for 5h;92%
With methanol; zinc(II) chloride
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

D-Glyceraldehyde-2-phosphate

D-Glyceraldehyde-2-phosphate

Conditions
ConditionsYield
With amidotriphosphate sodium salt; magnesium chloride at 20℃; for 120h; pH=7.1; Substitution;81%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

dihydroxyacetone
96-26-4

dihydroxyacetone

D-Fructose
57-48-7

D-Fructose

Conditions
ConditionsYield
With D-fructose-6-phosphate aldolase of Escherichia coli Ala129Ser mutant at 25℃; for 48h; pH=7.5; NaHCO3 buffer;81%
With transaldolase from listeria monocytogenes In aq. phosphate buffer for 8h; pH=7.5; Enzymatic reaction;25%
With E. coli transaldolase B mutant F178Y In glycyl-glycine buffer at 25℃; pH=8.5; Enzymatic reaction; optical yield given as %de; stereoselective reaction;
With E. coli transaldolase B mutant F178Y In glycyl-glycine buffer at 30℃; pH=8.5; Kinetics; Enzymatic reaction; stereoselective reaction;
indole
120-72-9

indole

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

C19H18N2O2

C19H18N2O2

Conditions
ConditionsYield
With montmorillonite K10 clay (K10) at 20℃; for 0.5h;80%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

allyl bromide
106-95-6

allyl bromide

1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol
164145-69-1

1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol

Conditions
ConditionsYield
With ammonium chloride; zinc In tetrahydrofuran at 0℃; for 6h;78%
fur-2-ylboronic acid
13331-23-2

fur-2-ylboronic acid

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

2-phenylacetylhydrazine
937-39-3

2-phenylacetylhydrazine

C15H18N2O4

C15H18N2O4

Conditions
ConditionsYield
In methanol at 25℃; for 24h; Petasis Reaction; diastereoselective reaction;77%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

1-deoxy-β-D-fructopyranose
119241-42-8

1-deoxy-β-D-fructopyranose

Conditions
ConditionsYield
With E. coli transaldolase B mutant F178Y In glycyl-glycine buffer at 25℃; pH=8.5; Enzymatic reaction; stereoselective reaction;75%
4-Fluorophenol
371-41-5

4-Fluorophenol

5,6-di-O-isopropylidene-(D)-mannitol

5,6-di-O-isopropylidene-(D)-mannitol

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

A

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate
64520-58-7

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

B

(2R)-2,3-epoxy-1-(4-fluorophenoxy)propane
104605-97-2

(2R)-2,3-epoxy-1-(4-fluorophenoxy)propane

Conditions
ConditionsYield
With sodium periodate; sodium sulfate In hexane; dichloromethane; sodium hydrogencarbonate; ethyl acetateA n/a
B 73%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

S,S'-((4-(2-aminoethoxy)-1,2-phenylene)bis(methylene)) diethanethioate hydrochloride

S,S'-((4-(2-aminoethoxy)-1,2-phenylene)bis(methylene)) diethanethioate hydrochloride

S,S'-((4-(2-(bis((S)-2,3-dihydroxypropyl)amino)ethoxy)-1,2-phenylene)bis(methylene)) diethanethioate hydrochloride

S,S'-((4-(2-(bis((S)-2,3-dihydroxypropyl)amino)ethoxy)-1,2-phenylene)bis(methylene)) diethanethioate hydrochloride

Conditions
ConditionsYield
Stage #1: D-Glyceraldehyde; S,S'-((4-(2-aminoethoxy)-1,2-phenylene)bis(methylene)) diethanethioate hydrochloride With sodium cyanoborohydride; acetic acid In methanol at 60℃; for 4h;
Stage #2: With hydrogenchloride In water pH=3;
72%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

calcium carbide
75-20-7

calcium carbide

dibenzylamine
103-49-1

dibenzylamine

N,N-dibenzyl-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-yn-1-amine
1510838-84-2

N,N-dibenzyl-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-yn-1-amine

Conditions
ConditionsYield
With copper(l) iodide In acetonitrile at 80℃; for 18h; Inert atmosphere;70%
N,N-dimethylisopropyl amine
996-35-0

N,N-dimethylisopropyl amine

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

[4-(tert-butoxycarbonylamino)phenyl]boronic acid
380430-49-9

[4-(tert-butoxycarbonylamino)phenyl]boronic acid

tert-butyl 4-((1S,2S)-2,3-dihydroxy-1-isopropyl(methyl)aminopropyl)-phenylcarbamate
1133434-00-0

tert-butyl 4-((1S,2S)-2,3-dihydroxy-1-isopropyl(methyl)aminopropyl)-phenylcarbamate

Conditions
ConditionsYield
In ethanol at 20℃; for 72h;69%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

1-deoxy-D-frucrose
32785-92-5

1-deoxy-D-frucrose

Conditions
ConditionsYield
With D-fructose-6-phosphate aldolase of Escherichia coli Ala129Ser mutant at 25℃; for 48h; pH=7.5; NaHCO3 buffer;68%
Conditions
ConditionsYield
With ethylenediaminetetraacetic acid In water for 48h; deoxyribose-5-phosphate aldolase (DERA), phosphate buffer, pH 7.3;65%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

calcium carbide
75-20-7

calcium carbide

diethylamine
109-89-7

diethylamine

1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-N,N-diethylprop-2-yn-1-amine
1510838-93-3

1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-N,N-diethylprop-2-yn-1-amine

Conditions
ConditionsYield
With copper(l) iodide In acetonitrile at 80℃; for 18h; Inert atmosphere;65%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

D-Serine
312-84-5

D-Serine

xylulose
551-84-8

xylulose

Conditions
ConditionsYield
With magnesium(II) chloride hexahydrate; flavin adenine dinucleotide (FAD)-containing flavoenzyme from the yeast Rhodotorula gracilis; thiamine pyrophosphate; oxygen In water at 25℃; for 8h; pH=7; Enzymatic reaction;65%
magnesium glycerol phosphate

magnesium glycerol phosphate

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

D-Fructose
57-48-7

D-Fructose

Conditions
ConditionsYield
Stage #1: magnesium glycerol phosphate; D-Glyceraldehyde With glycerol phosphate oxidase; recombinant D-fructose 1,6-bisphosphate aldolase from Staphylococcus carnosus; catalase In water at 20℃; for 22h; pH=7; Enzymatic reaction;
Stage #2: With hydrogenchloride; acid phosphatase from sweet potato In water at 37℃; for 24h; pH=Ca. 5; Enzymatic reaction; stereoselective reaction;
60%
With FAD; Staphylococcus carnosus D-fructose 1,6-bisphosphate aldolase; Streptococcus pneumonia glycerol phosphate oxidase In water-d2 at 30℃; for 22h; pH=7; Enzymatic reaction;56%
fur-2-ylboronic acid
13331-23-2

fur-2-ylboronic acid

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

N’-allyl-4-methoxybenzohydrazide
1354376-45-6

N’-allyl-4-methoxybenzohydrazide

C16H22N2O3

C16H22N2O3

Conditions
ConditionsYield
In dichloromethane at 25℃; for 24h; Petasis Reaction; diastereoselective reaction;58%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

3-hydroxy-2-oxopropionic acid
1113-60-6

3-hydroxy-2-oxopropionic acid

fructonic acid
669-90-9

fructonic acid

Conditions
ConditionsYield
With recombinant aldolase B2T1L6 from Burkholderia phytofirmans; manganese(ll) chloride In aq. buffer for 20h; pH=8; Catalytic behavior; Reagent/catalyst; Aldol Addition; Green chemistry; Enzymatic reaction; stereoselective reaction;55%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

2-isopropoxy-5-(3-(6-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-1,2,4-oxadiazol-5-yl)benzonitrile trifluoroacetate
1258856-14-2

2-isopropoxy-5-(3-(6-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-1,2,4-oxadiazol-5-yl)benzonitrile trifluoroacetate

(S)-5-(3-(3-(2,3-dihydroxypropyl)-6-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile hydrochloride
1258853-82-5

(S)-5-(3-(3-(2,3-dihydroxypropyl)-6-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile hydrochloride

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 92h; Inert atmosphere;47%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

2-[(1-methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride
1167415-61-3

2-[(1-methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride

5-(3-{3-[(2S)-2,3-dihydroxypropyl]-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl}-1,2,4-oxadiazol-5-yl)-2-[(1-methylethyl)oxy]benzonitrile
1258852-98-0

5-(3-{3-[(2S)-2,3-dihydroxypropyl]-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl}-1,2,4-oxadiazol-5-yl)-2-[(1-methylethyl)oxy]benzonitrile

Conditions
ConditionsYield
Stage #1: D-Glyceraldehyde; 2-[(1-methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 16h; Inert atmosphere;
Stage #2: D-Glyceraldehyde With acetic acid In dichloromethane
46%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

(2,4-dinitro-phenyl)-hydrazine
119-26-6

(2,4-dinitro-phenyl)-hydrazine

C9H10N4O6

C9H10N4O6

Conditions
ConditionsYield
In water at 20℃; for 24h;45%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

2-[(1-methylethyl)oxy]-5-[3-(5-methyl-1,2,3,4-tetrahydro-6-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride
1258855-37-6

2-[(1-methylethyl)oxy]-5-[3-(5-methyl-1,2,3,4-tetrahydro-6-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride

(S)-5-(3-(2-(2,3-dihydroxypropyl)-5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

(S)-5-(3-(2-(2,3-dihydroxypropyl)-5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 92h; Inert atmosphere;44%
D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

L-Cysteine
52-90-4

L-Cysteine

2(RS)-D-glycero-(1',2'-dihydroxyethyl)thiazolidine-4(R)-carboxylic acid
6851-62-3, 110224-40-3, 110224-41-4, 124617-03-4, 124617-05-6

2(RS)-D-glycero-(1',2'-dihydroxyethyl)thiazolidine-4(R)-carboxylic acid

Conditions
ConditionsYield
In water40.5%

453-17-8Relevant articles and documents

Electrochemical Activation of Galactose Oxidase: Mechanistic Studies and Synthetic Applications

Fryszkowska, Anna,Klapars, Artis,Marshall, Nicholas,Ruccolo, Serge,Strotman, Neil A.,Zhang, Shaoguang

, p. 7270 - 7280 (2021/06/30)

The enzyme galactose oxidase (GOase) is a copper radical oxidase that catalyzes the aerobic oxidation of primary alcohols to the aldehydes and has been utilized to that end in large-scale pharmaceutical processes. To maintain its catalytic activity and ensure high substrate conversion, GOase needs to be continuously (re)activated by 1e- oxidation of the constantly formed out-of-cycle species (GOasesemi) to the catalytically active state (GOaseox). In this work, we report an electrochemical activation method for GOase that replaces the previously used expensive horseradish peroxidase activator in a GOase-catalyzed oxidation reaction. First, the formation of GOaseox of a specifically engineered variant via nonenzymatic oxidation of GOasesemi was studied by UV-vis spectroscopy. Second, electrochemical oxidation of GOase by mediators was studied using cyclic voltammetry. The electron-transfer rates between GOase and various mediators at different pH values were determined, showing a dependence on both the redox potential of the mediator and the pH. This observation suggests that the oxidation of GOase by mediators at pH 7-9 likely occurs via a concerted proton-coupled electron-transfer (PCET) mechanism under anaerobic conditions. Finally, this electrochemical GOase activation method was successfully applied to the development of a bioelectrocatalytic GOase-mediated aerobic oxidation of benzyl alcohol derivatives, cinnamyl alcohol, and aliphatic polyols, including the desymmetrizing oxidation of 2-ethynylglycerol, a key step in the biocatalytic cascade used to prepare the promising HIV therapeutic islatravir.

Prebiotic synthesis of 2-deoxy-d-ribose from interstellar building blocks promoted by amino esters or amino nitriles

Steer, Andrew M.,Bia, Nicolas,Smith, David K.,Clarke, Paul A.

supporting information, p. 10362 - 10365 (2017/09/25)

Understanding the prebiotic genesis of 2-deoxy-d-ribose, which forms the backbone of DNA, is of crucial importance to unravelling the origins of life, yet remains open to debate. Here we demonstrate that 20 mol% of proteinogenic amino esters promote the selective formation of 2-deoxy-d-ribose over 2-deoxy-d-threopentose in combined yields of ≥4%. We also demonstrate the first aldol reaction promoted by prebiotically-relevant proteinogenic amino nitriles (20 mol%) for the enantioselective synthesis of d-glyceraldehyde with 6% ee, and its subsequent conversion into 2-deoxy-d-ribose in yields of ≥ 5%. Finally, we explore the combination of these two steps in a one-pot process using 20 mol% of an amino ester or amino nitrile promoter. It is hence demonstrated that three interstellar starting materials, when mixed together with an appropriate promoter, can directly lead to the formation of a mixture of higher carbohydrates, including 2-deoxy-d-ribose.

METHOD FOR PRODUCING CARBOHYDRATES FROM DIHYDROXYACETONE

-

Paragraph 00152, (2016/12/26)

The present invention relates to the use of dihydroxyacetone ("DHA") in the preparation of a number of natural and rare carbohydrates. The present invention comprises three stages. In the first stage of the present invention, syngas and formaldehyde are produced from natural gas, biogas, biomass and C02 from industrial plants including electricity generating plants, steel mills, cement factories and bio refineries. In the second stage of the present invention, formaldehyde and syngas from first stage are condensed to produce DHA. In the third stage of the present invention, DHA serves as a starting material for the synthesis of natural and rare carbohydrates using enzymes belonging to isomerase, aldolases, epimerase and transketolase groups.

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