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644-76-8 Usage

Chemical Properties

Light Beige Solid

Uses

1,6-Anhydro-β-D-glucopyranose is a carbohydrate contains in liquid smoke flavorings.

Check Digit Verification of cas no

The CAS Registry Mumber 644-76-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 4 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 644-76:
(5*6)+(4*4)+(3*4)+(2*7)+(1*6)=78
78 % 10 = 8
So 644-76-8 is a valid CAS Registry Number.

644-76-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,6-ANHYDRO-.β.-D-GALACTOPYRANOSE

1.2 Other means of identification

Product number -
Other names Levogalactosan

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:644-76-8 SDS

644-76-8Synthetic route

D-Galactose
10257-28-0

D-Galactose

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In water at 0℃; for 0.25h;99%
phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
2872-72-2

phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With sodium hydroxide for 120h; Heating;95%
With sodium hydroxide In water for 120h; Heating;95%
Pentachlorophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactose
91876-32-3

Pentachlorophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactose

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With potassium hydroxide for 1h; Heating;75%
1,6-anhydro-2,3,4-tri-O-benzyl-β-D-galactopyranose
29704-64-1

1,6-anhydro-2,3,4-tri-O-benzyl-β-D-galactopyranose

A

1,6-anhydro-3-O-benzoyl-2-O-benzyl-β-D-galactopyranose
104477-44-3

1,6-anhydro-3-O-benzoyl-2-O-benzyl-β-D-galactopyranose

B

1,6-anhydro-3-O-benzoyl-β-D-galactopyranose
71019-57-3

1,6-anhydro-3-O-benzoyl-β-D-galactopyranose

C

1,6-anhydro-3,4-di-O-benzyl-β-D-galactopyranose
66963-43-7

1,6-anhydro-3,4-di-O-benzyl-β-D-galactopyranose

D

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
palladium on activated charcoal In isopropyl alcohol for 5h; Heating; further O-benzyl protecting 1,6-anhydrohexoses, various reaction time;A n/a
B 70%
C 40%
D n/a
1,6-anhydro-2,3,4-tri-O-benzyl-β-D-galactopyranose
29704-64-1

1,6-anhydro-2,3,4-tri-O-benzyl-β-D-galactopyranose

A

1,6-anhydro-3-O-benzoyl-β-D-galactopyranose
71019-57-3

1,6-anhydro-3-O-benzoyl-β-D-galactopyranose

B

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
palladium on activated charcoal In isopropyl alcohol for 5h; Heating;A 70%
B n/a
With isopropyl alcohol; palladium on activated charcoal for 5h; Heating;A 70%
B n/a
1,6-anhydro-2,3,4-tri-O-acetyl-β-D-galactopyranose
4132-24-5

1,6-anhydro-2,3,4-tri-O-acetyl-β-D-galactopyranose

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 15h; Ambient temperature;59%
With sodium methylate
3-(β-D-galactopyranosyloxy)-2-furanyl methyl ketone
82756-28-3

3-(β-D-galactopyranosyloxy)-2-furanyl methyl ketone

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With pyrrolidine; triethylamine In ethanol at 79 - 80℃; for 24h;41%
β-D-galactopyranoside
7296-64-2

β-D-galactopyranoside

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
at 360℃; under 0.1 Torr;
D-Galactose
59-23-4

D-Galactose

A

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

B

1,6-Anhydro-α-D-galactofuranose
33818-21-2

1,6-Anhydro-α-D-galactofuranose

Conditions
ConditionsYield
under 15 Torr;
With sulfuric acid
at 265 - 375℃; under 2 Torr; α-D-Galactopyranose;
D-Galactose
59-23-4

D-Galactose

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
at 360℃; under 0.1 Torr; β-D-Galactopyranose;
trimethyl-(tetra-O-acetyl-β-D-galactopyranosyl)-ammonium; bromide
60583-05-3

trimethyl-(tetra-O-acetyl-β-D-galactopyranosyl)-ammonium; bromide

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With barium dihydroxide; water
β-D-galactopyranosyl fluoride
2021-62-7

β-D-galactopyranosyl fluoride

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With barium dihydroxide; water
1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose
52579-97-2

1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With hydrogenchloride
phenyl-β-D-galactopyranoside
2818-58-8

phenyl-β-D-galactopyranoside

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With potassium hydroxide
LACTOSE
5965-66-2

LACTOSE

A

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

B

levoglucosan
498-07-7

levoglucosan

Conditions
ConditionsYield
under 15 Torr; Erhitzen;
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside
3068-32-4

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With potassium phenolate; phenol Erwaermen des Reaktionsprodukts mit wss. Kalilauge;
Multi-step reaction with 2 steps
1: 85 percent / acetone / 2 h / Heating
2: 75 percent / aq. KOH / 1 h / Heating
View Scheme
2-O-(benzoyl)-1,6-anhydro-3,4-dideoxy-β-D-erythro-hex-3-enopyranose
67307-86-2

2-O-(benzoyl)-1,6-anhydro-3,4-dideoxy-β-D-erythro-hex-3-enopyranose

A

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

B

1,6-anhydro-β-D-glucopyranoside
14059-68-8

1,6-anhydro-β-D-glucopyranoside

Conditions
ConditionsYield
With ammonium hydroxide; osmium(VIII) oxide; 4-methylmorpholine N-oxide 1.) acetone, H2O, RT, 20 h, 2.) CH3OH, RT, overnight; var. 2-O-acyl protected 1,6-anhydro-3,4-dideoxy-β-D-erythro-hex-3-enopyranoses;
1,6-anhydro-β-D-galactopyranose
125164-19-4

1,6-anhydro-β-D-galactopyranose

A

1,6-anhydro-3-O-butanoyl-β-D-galactopyranose
128333-92-6

1,6-anhydro-3-O-butanoyl-β-D-galactopyranose

B

1,6-anhydro-4-O-butanoyl-β-D-galactopyranose
128333-91-5

1,6-anhydro-4-O-butanoyl-β-D-galactopyranose

C

1,6-anhydro-3,4-di-O-butanoyl-β-D-galactopyranose
125164-20-7

1,6-anhydro-3,4-di-O-butanoyl-β-D-galactopyranose

D

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With enzymes from C. cylindracea; Pancreas Product distribution; different times;
1,6-anhydro-3,4-O-<5-(hydroxymethyl)-2-furfurylidene>-β-D-galactopyranose
95881-40-6

1,6-anhydro-3,4-O-<5-(hydroxymethyl)-2-furfurylidene>-β-D-galactopyranose

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

(2,4-dinitro-phenyl)-hydrazine

A

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

B

5-(hydroxymetyl)-2-furaldehyde 2,4-dinitrophenylhydrazone
15465-62-0

5-(hydroxymetyl)-2-furaldehyde 2,4-dinitrophenylhydrazone

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.5h; Ambient temperature;
(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-phenoxytetrahydro-2H-pyran-3,4,5-triyl triacetate
18463-30-4

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-phenoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With sodium hydroxide at 100℃;
sodium methylate
124-41-4

sodium methylate

1-O-tosyl-2,3,4,6-tetra-O-acetyl-D-galactopyranose

1-O-tosyl-2,3,4,6-tetra-O-acetyl-D-galactopyranose

A

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

B

methyl beta-D-galactopyranoside
1824-94-8

methyl beta-D-galactopyranoside

C

methyl α-D-galactopyranoside
3396-99-4

methyl α-D-galactopyranoside

Conditions
ConditionsYield
In pyridine; methanol at 80℃; for 2.5h;
1-O-tosyl-2,3,4,6-tetra-O-acetyl-D-galactopyranose

1-O-tosyl-2,3,4,6-tetra-O-acetyl-D-galactopyranose

A

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

B

methyl beta-D-galactopyranoside
1824-94-8

methyl beta-D-galactopyranoside

C

methyl α-D-galactopyranoside
3396-99-4

methyl α-D-galactopyranoside

Conditions
ConditionsYield
With sodium methylate In pyridine; methanol at 80℃; for 2.5h;
water
7732-18-5

water

β-D-galactopyranosyl fluoride
2021-62-7

β-D-galactopyranosyl fluoride

barium hydroxide

barium hydroxide

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

D-Galactose
59-23-4

D-Galactose

sulfuric acid
7664-93-9

sulfuric acid

A

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

B

1,6-Anhydro-α-D-galactofuranose
33818-21-2

1,6-Anhydro-α-D-galactofuranose

water
7732-18-5

water

trimethyl-(tetra-O-acetyl-β-D-galactopyranosyl)-ammonium; bromide
60583-05-3

trimethyl-(tetra-O-acetyl-β-D-galactopyranosyl)-ammonium; bromide

barium hydroxide

barium hydroxide

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

β-D-galactose peracetate
4163-60-4

β-D-galactose peracetate

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: p-TsOH / 1.5 h / 90 °C / 15 Torr
2: 95 percent / NaOH / H2O / 120 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 77 percent / p-toluenesulfonic acid / 1.5 h / 95 °C / 15 Torr
2: 95 percent / aq. NaOH / 120 h / Heating
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: MeONa / methanol; pyridine / 2.5 h / 80 °C
View Scheme
2,3,4,6-tetra-O-acetyl-β-galactopyranosyl fluoride
4163-45-5

2,3,4,6-tetra-O-acetyl-β-galactopyranosyl fluoride

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium methylate; methanol
2: barium hydroxide; water
View Scheme
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

1,6-Anhydro-β-D-xylo-hexapyranose-3-ulose
2595-18-8

1,6-Anhydro-β-D-xylo-hexapyranose-3-ulose

Conditions
ConditionsYield
With phenyltrimethylammonium tribromide; potassium carbonate In tetrahydrofuran; methanol at 20℃; for 4h; Solvent; regioselective reaction;99%
With p-benzoquinone In [D3]acetonitrile at 50℃; for 1h; Solvent; chemoselective reaction;80 %Spectr.
triethylsilyl chloride
994-30-9

triethylsilyl chloride

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

C12H24O5Si
1452154-12-9

C12H24O5Si

Conditions
ConditionsYield
With (2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine; N,N-diisopropylethylamine hydrochloride; N-ethyl-N,N-diisopropylamine for 4h; regioselective reaction;98%
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

1,6-anhydro-4-O-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranoside
1330004-27-7

1,6-anhydro-4-O-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranoside

Conditions
ConditionsYield
Stage #1: 1,6-anhydro-β-D-galactopyranose With diphenyltin(IV) dichloride In acetonitrile at 20℃; for 0.166667h;
Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide With 5,5'-dimethyl-2,2'-bipyridine; silver(l) oxide In acetonitrile at 20 - 35℃; for 24h; Koenigs-Knorr Glycosidation; stereoselective reaction;
96%
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 60℃; for 16h; Koenigs-Knorr synthesis; Inert atmosphere; regioselective reaction;73%
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

1,6-anhydro-β-D-galactopyranose 3,4-ethoxyacetal
128790-77-2

1,6-anhydro-β-D-galactopyranose 3,4-ethoxyacetal

Conditions
ConditionsYield
With sulfonic acid In N,N-dimethyl-formamide for 12h; Ambient temperature;95%
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

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

2,2-dimethoxy-propane

1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose
52579-97-2

1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 1h; Ambient temperature;95%
With toluene-4-sulfonic acid In acetone for 16h; Ambient temperature;79%
With toluene-4-sulfonic acid In acetone ketalization;
acetic anhydride
108-24-7

acetic anhydride

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

D-galactose pentaacetate
25878-60-8

D-galactose pentaacetate

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) at 20℃; for 5h;95%
benzoyl chloride
98-88-4

benzoyl chloride

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

1,6-Anhydro-2,3,4-tri-O-benzoyl-β-D-galactopyranose
91876-33-4

1,6-Anhydro-2,3,4-tri-O-benzoyl-β-D-galactopyranose

Conditions
ConditionsYield
With pyridine94%
With pyridine
benzyl bromide
100-39-0

benzyl bromide

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

1,6-anhydro-4-O-benzyl-β-D-galactopyranoside
116836-98-7

1,6-anhydro-4-O-benzyl-β-D-galactopyranoside

Conditions
ConditionsYield
With 3 A molecular sieve; bis(tri-n-butyltin)oxide; 1-methyl-1H-imidazole; tetra-(n-butyl)ammonium iodide In toluene 1.) reflux, 15 h; 2.) 1.5 h;93%
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

acetyl chloride
75-36-5

acetyl chloride

4-O-acetyl-1,6-anhydro-β-D-galactopyranose
128333-94-8

4-O-acetyl-1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With (2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine; N,N-diisopropylethylamine hydrochloride; N-ethyl-N,N-diisopropylamine for 4h; regioselective reaction;93%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

C7H12O7S
1452154-26-5

C7H12O7S

Conditions
ConditionsYield
With (2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine; N,N-diisopropylethylamine hydrochloride; N-ethyl-N,N-diisopropylamine for 4h; regioselective reaction;88%
benzyl bromide
100-39-0

benzyl bromide

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

A

1,6-anhydro-3-O-benzyl-β-D-galactopyranoside
76819-15-3

1,6-anhydro-3-O-benzyl-β-D-galactopyranoside

B

1,6-anhydro-4-O-benzyl-β-D-galactopyranoside
116836-98-7

1,6-anhydro-4-O-benzyl-β-D-galactopyranoside

Conditions
ConditionsYield
With tetrabutylammomium bromide; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine In neat (no solvent) at 70℃; for 3.5h; regioselective reaction;A 10%
B 87%
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 40℃; for 48h; Inert atmosphere; regioselective reaction;A n/a
B 73%
With 3 A molecular sieve; bis(tri-n-butyltin)oxide; 1-methyl-1H-imidazole In toluene Product distribution; effect of the other catalyst (tetrabutylammonium halide) and reaction time;
With 3 A molecular sieve; bis(tri-n-butyltin)oxide; 1-methyl-1H-imidazole; tetrabutylammomium bromide In toluene 1.) reflux, 15 h; 2.) 7 h;A 20 % Chromat.
B 80 % Chromat.
tert-butyldimethylsilane
29681-57-0

tert-butyldimethylsilane

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

A

2,4-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

2,4-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

B

2,3-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

2,3-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

C

2,3,4-tris(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

2,3,4-tris(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

Conditions
ConditionsYield
With [Ir(COD)(PPh3)2]SbF6 In N,N-dimethyl acetamide at 70℃;A 87%
B 4%
C 6%
C36H40O5Si

C36H40O5Si

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

A

C42H50O10Si

C42H50O10Si

B

C42H50O10Si

C42H50O10Si

Conditions
ConditionsYield
With 4-nitrophenylboronic acid In acetonitrile at 0℃; for 2h; Temperature; Inert atmosphere;A 87%
B 10%
p-Anisaldehyde dimethyl acetal
2186-92-7

p-Anisaldehyde dimethyl acetal

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

1,6-anhydro-endo-3,4-O-(4-methoxybenzylidene)-β-D-galactopyranose
157886-59-4

1,6-anhydro-endo-3,4-O-(4-methoxybenzylidene)-β-D-galactopyranose

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 25℃; for 3h;86%
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

1,6-anhydro-3-O-(4-toluenesulfonyl)-β-D-galactopyranoside
1372890-67-9

1,6-anhydro-3-O-(4-toluenesulfonyl)-β-D-galactopyranoside

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; 2-((R)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 48h; regioselective reaction;84%
With 2-Aminoethoxydiphenylborane; N-ethyl-N,N-diisopropylamine In acetonitrile at 23℃; for 48h; Inert atmosphere; regioselective reaction;83%
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

4-Methoxybenzaldehyde dipent-4-enyl acetal
157886-54-9

4-Methoxybenzaldehyde dipent-4-enyl acetal

(1R,2S,6R,7R,8R)-4-(4-Methoxy-phenyl)-3,5,9,11-tetraoxa-tricyclo[6.2.1.02,6]undecan-7-ol

(1R,2S,6R,7R,8R)-4-(4-Methoxy-phenyl)-3,5,9,11-tetraoxa-tricyclo[6.2.1.02,6]undecan-7-ol

Conditions
ConditionsYield
With N-Bromosuccinimide; camphor-10-sulfonic acid In acetonitrile for 0.25h; Ambient temperature;82%
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

4-Methoxybenzaldehyde dipent-4-enyl acetal
157886-54-9

4-Methoxybenzaldehyde dipent-4-enyl acetal

1,6-Anhydro-endo-3,4-O-(4-methoxybenzylidene)-β-D-galactopyranose

1,6-Anhydro-endo-3,4-O-(4-methoxybenzylidene)-β-D-galactopyranose

Conditions
ConditionsYield
With N-Bromosuccinimide; camphor-10-sulfonic acid In acetonitrile for 0.25h; Ambient temperature;82%
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

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

2,2-dimethoxy-propane

1,6-anhydro-3,4-O-isopropylidene-β-D-galactose

1,6-anhydro-3,4-O-isopropylidene-β-D-galactose

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran81%
benzaldehyde
100-52-7

benzaldehyde

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

1,6-anhydro-3,4-O-(S)-benzylidene-β-D-galactopyranose
71021-25-5

1,6-anhydro-3,4-O-(S)-benzylidene-β-D-galactopyranose

Conditions
ConditionsYield
With zinc(II) chloride78%
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

2-bromomethylnaphthyl bromide
939-26-4

2-bromomethylnaphthyl bromide

A

1,6-anhydro-4-O-(2-naphthyl)methyl-β-D-galactopyranoside
1309382-52-2

1,6-anhydro-4-O-(2-naphthyl)methyl-β-D-galactopyranoside

B

1,6-anhydro-3-O-(2-naphthyl)methyl-β-D-galactopyranoside

1,6-anhydro-3-O-(2-naphthyl)methyl-β-D-galactopyranoside

Conditions
ConditionsYield
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 40℃; for 48h; Inert atmosphere; regioselective reaction;A 74%
B n/a
1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

polymer, Mw 26900 by static laser light scattering; monomer(s): 1,6-anhydro-β-D-galactopyranose

polymer, Mw 26900 by static laser light scattering; monomer(s): 1,6-anhydro-β-D-galactopyranose

Conditions
ConditionsYield
With (S-2-butenyl)tetramethylenesulfonium hexafluoroantimonate In various solvent(s) at 150℃; for 0.666667h;63.1%
Benzyloxymethyl chloride
3587-60-8

Benzyloxymethyl chloride

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

A

1,6-anhydro-4-O-benzyloxymethyl-β-D-galactopyranoside
1309382-53-3

1,6-anhydro-4-O-benzyloxymethyl-β-D-galactopyranoside

B

1,6-anhydro-3-O-benzyloxymethyl-β-D-galactopyranoside

1,6-anhydro-3-O-benzyloxymethyl-β-D-galactopyranoside

Conditions
ConditionsYield
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 40℃; for 48h; Inert atmosphere; regioselective reaction;A 63%
B n/a
tert-butyldimethylsilane
29681-57-0

tert-butyldimethylsilane

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

A

2,4-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

2,4-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

B

2,3-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

2,3-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

C

(1R,2S,3R,4R,5R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-6,8-dioxa-bicyclo[3.2.1]octan-4-ol

(1R,2S,3R,4R,5R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-6,8-dioxa-bicyclo[3.2.1]octan-4-ol

D

2,3,4-tris(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

2,3,4-tris(t-butyldimethylsilyl)-1,6-anhydro-β-D-galactose

Conditions
ConditionsYield
With [Rh(COD)(PPh3)2]SbF6 In N,N-dimethyl acetamide at 70℃;A 62%
B 22%
C 3%
D 6%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

1,6-anhydro-β-D-galactopyranose
644-76-8

1,6-anhydro-β-D-galactopyranose

1,6-anhydro-endo-3,4-O-benzylidene-β-D-galactopyranose
93451-82-2

1,6-anhydro-endo-3,4-O-benzylidene-β-D-galactopyranose

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide58%

644-76-8Relevant articles and documents

-

Fernez,Stoffyn

, p. 139,141 (1959)

-

High-pressure fast-pyrolysis, fast-hydropyrolysis and catalytic hydrodeoxygenation of cellulose: Production of liquid fuel from biomass

Venkatakrishnan, Vinod Kumar,Degenstein, John C.,Smeltz, Andrew D.,Delgass, W. Nicholas,Agrawal, Rakesh,Ribeiro, Fabio H.

, p. 792 - 802 (2014/02/14)

A lab-scale, high-pressure, continuous-flow fast-hydropyrolysis and vapor-phase catalytic hydrodeoxygenation (HDO) reactor has been successfully designed, built and tested with cellulose as a model biomass feedstock. We investigated the effects of pyrolysis temperature on high-pressure cellulose fast-pyrolysis, hydrogen on high-pressure cellulose fast-hydropyrolysis, reaction pressure (27 bar and 54 bar) on our reactor performance and candidate catalysts for downstream catalytic HDO of cellulose fast-hydropyrolysis vapors. In this work, a liquid chromatography-mass spectrometry (LC-MS) method has been developed and utilized for quantitative characterization of the liquid products. The major compounds in the liquid from cellulose fast-pyrolysis (27 bar, 520 °C) are levoglucosan and its isomers, formic acid, glycolaldehyde, and water, constituting 51 wt%, 11 wt%, 8 wt% and 24 wt% of liquid respectively. Our results show that high pressures of hydrogen do not have a significant effect on the fast-hydropyrolysis of cellulose at 480 °C but suppress the formation of reactive light oxygenate species like glycolaldehyde and formic acid at 580 °C. The formation of permanent gases (CO, CO2, CH4) and glycolaldehyde and formic acid increased with increasing pyrolysis temperature in the range of 480 °C-580 °C in high-pressure cellulose fast-pyrolysis, in the absence of hydrogen. Candidate HDO catalysts Al 2O3, 2% Ru/Al2O3 and 2% Pt/Al 2O3 resulted in extents of deoxygenation of 20%, 22% and 27%, respectively, but led to carbon loss to gas phase as CO and CH4. These catalysts provide useful insights for other candidate HDO catalysts for improving the extent of deoxygenation with higher carbon recovery in the liquid product.

On the regioselective acylation of 1,6-anhydro-β-D- and L-hexopyranoses catalysed by lipases: Structural bass and synthetic applications

Boissière-Junot, Nathalie,Tellier, Charles,Rabiller, Claude

, p. 99 - 115 (2007/10/03)

With the aim of providing new methods for the regioselective protection at the 2,3 and 4 positions of monosaccharides, we have studied the acetylation of a class of rigid sugars: the 1,6-anhydro-β-D- and L-hexopyranoses (hexopyranosanes D-1 to D-5 and L-1 to L-5), using vinyl acetate as an acyl donor and two common lipases,Candida rugosa and Pseudomonas cepacia, as catalysts. Our results indicate that the relative orientation of the hydroxyls governs the regioselectivity of acetylation. In the D-series, when the 3-OH is in the axial position, acetylation occurs mainly at the 4-axial OH, while the 2-axial OH is preferred when the 4-OH is equatorial. Conversely, when the 3-OH is equatorial, a strong selectivity affects the equatorial 2-OH. Compounds of the L-series were shown to be poor substrates for the lipase Pseudomonas cepacia except for L-galactosane for which the 2-monoacetyl ester was obtained in good yield. An attempt to rationalize the results by means of molecular modelling is also made to account for the catalytic activity of the Candida rugosa lipase on hexopyranosanes 1-3.

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