beta-D-Galactose pentaacetate supplier

Name
beta-D-Galactose pentaacetate
EINECS 224-008-0
CAS No. 4163-60-4
Article Data105
CAS DataBase
Density 1.3 g/cm³
Solubility methanol: 50 mg/mL, clear
Melting Point 143-144 °C(lit.)
Formula C₁₆H₂₂O₁₁
Boiling Point 434.8 °C at 760 mmHg
Molecular Weight 390.344
Flash Point 188.1 °C
Transport Information
Appearance white fine crystalline powder
Safety 24/25-36/37/39-27-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Galactopyranose,pentaacetate, b-D-(8CI);b-D-Galactopyranose, pentaacetate(9CI);1,2,3,4,6-Penta-O-acetyl-b-D-galactopyranose;1,2,3,4,6-Penta-O-acetyl-b-D-galactopyranoside;1,2,3,4,6-Penta-O-acetyl-b-D-galactose;2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl acetate;NSC 119334;NSC 1353;Penta-O-acetyl-b-D-galactopyranose;Pentaacetyl-b-D-galactose;b-Pentaacetylgalactose;
PSA 140.73000
LogP -0.36740

Synthetic route

: 59-23-4
D-Galactose

: 108-24-7
acetic anhydride

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
With pyridine; dmap at 20℃; Inert atmosphere;	100%
With iodine for 2h; cooling;	98.6%
With sodium thiocyanide

: 7296-64-2
β-D-galactopyranoside

: 108-24-7
acetic anhydride

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
With sodium acetate at 120℃; for 1h;	96%
Stage #1: acetic anhydride With sodium acetate at 100℃; for 0.5h; Stage #2: β-D-galactopyranoside at 100℃; for 1h;	96%
With pyridine at 20℃; for 24h;	95%

: 10257-28-0
D-Galactose

: 108-24-7
acetic anhydride

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
sulfuric acid at 20℃; for 0.0833333h; sonication;	94%
With sodium acetate at 120℃;	94%
With sodium acetate for 0.00555556h; microwave irradiation;	92%

: 3254-15-7
3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose

: 64-19-7
acetic acid

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
for 1h;	92.6%

: 492-62-6
alpha-D-glucopyranose

: 108-24-7
acetic anhydride

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
With sodium acetate at 100 - 130℃; under 760.051 Torr; for 4h; Large scale;	92.5%

: 10257-28-0
D-Galactose

: 127-09-3
sodium acetate

: 108-24-7
acetic anhydride

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
for 4h; Reflux;	92%
for 1h; Heating;	81%
for 1h;	81%
at 60℃; for 6h;	67%
at 100℃; for 0.333333h;	38%

...Expand

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

: 4098-06-0
triacetyl-D-galactal

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -45 - -25℃; for 1h;	89%

: 50801-29-1
3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-α-D-galactopyranose

: 2754-27-0
trimethylsilyl acetate

A: 130583-14-1
1,3,4,6-tetra-O-acetyl-2-O-trimethylsilyl-β-D-galactopyranose

B: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
at 107℃;	A 14% B 83%

...Expand

: 7296-64-2
β-D-galactopyranoside

: 127-09-3
sodium acetate

: 108-24-7
acetic anhydride

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
at 50 - 90℃; for 2.5h;	83%
at 130℃;	82%
for 3h; Reflux;	53%

...Expand

: 2280-44-6
D-Glucose

: 108-24-7
acetic anhydride

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
With iodine Reagent/catalyst;	70%

: 10257-28-0
D-Galactose

: 108-24-7
acetic anhydride

A: 4163-60-4
β-D-galactose peracetate

B: 83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5
penta-O-acetyl-α-D-galactopyranose

C: 5531-53-3, 10535-09-8, 22435-12-7, 40031-23-0, 55123-31-4, 62181-82-2, 72002-47-2, 72691-27-1, 72691-28-2
1,2,3,5,6-penta-O-acetyl-β-D-galactofuranose

D: 5531-53-3, 10535-09-8, 22435-12-7, 40031-23-0, 55123-31-4, 62181-82-2, 72002-47-2, 72691-27-1, 72691-28-2
1,2,3,5,6-penta-O-acetyl-4-thio-α-D-galactofuranose

Conditions

Conditions	Yield
Stage #1: D-Galactose; acetic anhydride With sodium acetate at 100℃; Inert atmosphere; Stage #2: With dmap at 100℃;	A 60% B n/a C n/a D n/a
With H-Beta zeolite for 8h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With sulfuric acid In acetic acid at 50℃; for 3h; Acetylation; Title compound not separated from byproducts.;

...Expand

: 1130007-82-7
1,2,3,5,6-penta-O-tert-butyldimethylsilyl-β-D-galactofuranose

: 108-24-7
acetic anhydride

A: 10356-82-8, 118380-74-8, 17296-20-7
1,1,2,3,4,5,6-hepta-O-acetylaldehydo-D-glucose aldehydrol

B: 5531-53-3, 10535-09-8, 22435-12-7, 40031-23-0, 55123-31-4, 72002-47-2, 72691-27-1, 72691-28-2, 62181-82-2
1,2,3,5,6-penta-O-acetyl-α,β-D-galactofuranose

C: 4163-60-4
β-D-galactose peracetate

D: 83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5
penta-O-acetyl-α-D-galactopyranose

Conditions

Conditions	Yield
With sulfuric acid In dichloromethane at 20℃; for 1h; Inert atmosphere; optical yield given as %de;	A 8% B 58% C n/a D n/a

...Expand

: 7296-64-2
β-D-galactopyranoside

: 127-09-3
sodium acetate

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
In methanol; acetic anhydride at 140℃;	52.3%

: 10257-28-0
D-Galactose

: 127-09-3
sodium acetate

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
In acetic anhydride Reflux;	47%
In acetic anhydride at 120℃; for 1.3h;

: 75-36-5
acetyl chloride

: 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

A: 4163-60-4
β-D-galactose peracetate

B: 6806-56-0
2,3,4,6-tetra-O-acetyl-1S-acetyl-1-thio-β-D-galactopyranose

Conditions

Conditions	Yield
With silver tetrafluoroborate In dichloromethane	A n/a B 35%

...Expand

: 108-24-7
acetic anhydride

: 2-(β-D-galactopyranosyl)hydrazinecarbothioamide

A: 13053-83-3
N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide

: 71952-23-3, 72002-46-1, 115510-62-8
(-)-5-acetamido-3-N-acetyl-2-(1,2,3,4,5-penta-O-acetyl-D-galacto-pentitol-1-yl)-1,3,4-thiadiazoline

C: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
for 4h; Product distribution; Cyclization; acetylation; Heating;	A n/a B 26% C n/a
for 4h; Cyclization; acetylation; Heating;	A n/a B 26% C n/a

...Expand

: 59-23-4
D-Galactose

: 108-24-7
acetic anhydride

A: 4163-60-4
β-D-galactose peracetate

B: 5531-53-3, 10535-09-8, 22435-12-7, 40031-23-0, 55123-31-4, 62181-82-2, 72002-47-2, 72691-27-1, 72691-28-2
1,2,3,5,6-penta-O-acetyl-β-D-galactofuranose

Conditions

Conditions	Yield
With pyridine

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 108-24-7
acetic anhydride

: O-(2,3,4-Tri-O-acetyl-β-D-galactopyranosiduronamid)-(1-4)-2-acetamido-1,3-di-O-acetyl-2,6-didesoxy-α-D-glucopyranose

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
Multistep reaction;

...Expand

: 10257-28-0
D-Galactose

: 4163-60-4
β-D-galactose peracetate

: 103082-76-4
2'-trimethylsilylethanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

: 108-24-7
acetic anhydride

A: 4163-60-4
β-D-galactose peracetate

B: 83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5
penta-O-acetyl-α-D-galactopyranose

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In toluene for 2h; Ambient temperature; Yield given. Yields of byproduct given;
With boron trifluoride diethyl etherate In toluene at 22℃; for 2h; Yield given. Yields of byproduct given;
With boron trifluoride diethyl etherate In toluene at 22℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 108-24-7
acetic anhydride

: 3396-99-4
methyl α-D-galactopyranoside

A: 118380-74-8
1,1,2,3,4,5,6-hepta-O-acetyl-aldehydo-D-galactose aldehydrol

B: 5531-53-3, 10535-09-8, 22435-12-7, 40031-23-0, 55123-31-4, 62181-82-2, 72002-47-2, 72691-27-1, 72691-28-2
Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester

C: 4163-60-4
β-D-galactose peracetate

D: 83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5
penta-O-acetyl-α-D-galactopyranose

Conditions

Conditions	Yield
With iron(III) chloride at 60℃; for 3h; Title compound not separated from byproducts;	A 13.6 % Chromat. B n/a C n/a D 58.8 % Chromat.

...Expand

: 70191-05-8
2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

: 108-24-7
acetic anhydride

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
Yield given;

: 59-23-4
D-Galactose

: 108-24-7
acetic anhydride

A: 4163-60-4
β-D-galactose peracetate

B: 83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5
penta-O-acetyl-α-D-galactopyranose

C: 5531-53-3, 10535-09-8, 22435-12-7, 40031-23-0, 55123-31-4, 62181-82-2, 72002-47-2, 72691-27-1, 72691-28-2
1,2,3,5,6-penta-O-acetyl-β-D-galactofuranose

D: 5531-53-3, 10535-09-8, 22435-12-7, 40031-23-0, 55123-31-4, 62181-82-2, 72002-47-2, 72691-27-1, 72691-28-2
1,2,3,5,6-penta-O-acetyl-4-thio-α-D-galactofuranose

Conditions

Conditions	Yield
montmorillonite K-10 for 10h; Ambient temperature;	A 20 % Spectr. B 55 % Spectr. C 17 % Spectr. D 8 % Spectr.

...Expand

: 10257-28-0
D-Galactose

: 108-24-7
acetic anhydride

A: 4163-60-4
β-D-galactose peracetate

B: 83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5
penta-O-acetyl-α-D-galactopyranose

Conditions

Conditions	Yield
With sodium acetate at 137℃; for 0.183333h; Acetylation; microwave irradiation;	A 6.78 g B 4.52 g
With iodine at 20℃; for 0.133333h; Acetylation;
With pyridine cooling;

...Expand

agarose acetate: agarose acetate

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 108-24-7
acetic anhydride

D-galacetose: D-galacetose

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
With sodium acetate

: 10257-28-0
D-Galactose

: 108-24-7
acetic anhydride

A: 118380-74-8
1,1,2,3,4,5,6-hepta-O-acetyl-aldehydo-D-galactose aldehydrol

B: 4163-60-4
β-D-galactose peracetate

C: 83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5
penta-O-acetyl-α-D-galactopyranose

D: 5531-53-3, 10535-09-8, 22435-12-7, 40031-23-0, 55123-31-4, 62181-82-2, 72002-47-2, 72691-27-1, 72691-28-2
1,2,3,5,6-penta-O-acetyl-β-D-galactofuranose

Conditions

Conditions	Yield
Stage #1: D-Galactose With boric acid In acetic acid at 50℃; for 1h; Cyclization; Stage #2: acetic anhydride With sulfuric acid In acetic acid at 50℃; for 3h; Acetylation; Further stages. Further byproducts. Title compound not separated from byproducts.;

...Expand

: Acetic acid (2R,3S,4R,5R)-4-acetoxy-2-acetoxymethyl-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

: 108-24-7
acetic anhydride

A: 4163-60-4
β-D-galactose peracetate

B: 83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5
penta-O-acetyl-α-D-galactopyranose

Conditions

Conditions	Yield
With pyridine Title compound not separated from byproducts;

...Expand

: 3068-32-4
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

: 4163-60-4
β-D-galactose peracetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaH / dimethylformamide 2: AgBF4 / CH2Cl2 View Scheme

: 4163-60-4
β-D-galactose peracetate

: 3068-32-4
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 0 - 20℃;	100%
With hydrogen bromide In dichloromethane	100%
With bismuth(III) bromide; triethyl-bromo-silane In dichloromethane at 20℃; for 3h;	100%

: 4163-60-4
β-D-galactose peracetate

: 13992-26-2
(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions

Conditions	Yield
With trimethylsilylazide; silver perchlorate; tin(IV) chloride In dichloromethane; toluene for 3h; Ambient temperature;	100%
With trimethylsilylazide; tin(IV) chloride In dichloromethane at 20℃; for 1h;	100%
Stage #1: β-D-galactose peracetate With trimethylsilylazide In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With tin(IV) chloride In dichloromethane at 20℃; Inert atmosphere;	98%

: 4163-60-4
β-D-galactose peracetate

: 3947-62-4, 6207-76-7, 10343-06-3, 19235-21-3, 22554-70-7, 22860-22-6, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 47339-09-3
2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

Conditions

Conditions	Yield
With hydrazinium monoacetate In N,N-dimethyl-formamide at 55℃; for 0.25h; Deacetylation;	100%
With hydrazinium monoacetate In N,N-dimethyl-formamide at 50℃; for 2h; chemoselective reaction;	96%
With hydrazinium monoacetate In N,N-dimethyl-formamide at 20℃;	96%

: 4163-60-4
β-D-galactose peracetate

: 75801-94-4
tetra-O-acetyl-α-iodogalactopyranose

Conditions

Conditions	Yield
With trimethylsilyl iodide In dichloromethane Inert atmosphere;	100%
With triethylsilane; iodine In dichloromethane at 0℃; for 2h; Heating;	91%
With trimethylsilyl iodide In toluene at 80℃; for 0.5h;	77%

: 108-98-5
thiophenol

: 4163-60-4
β-D-galactose peracetate

: 13992-16-0, 23661-28-1, 28512-68-7, 65236-85-3, 86782-39-0, 108032-93-5, 121524-01-4, 121570-34-1, 24404-53-3
1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0℃;	100%
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 2h; Inert atmosphere;	99%
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 12h;	98%

: 107-19-7
propargyl alcohol

: 4163-60-4
β-D-galactose peracetate

: 211688-84-5
2-propynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;	100%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 48h; Inert atmosphere;	100%
With boron trifluoride diethyl etherate In dichloromethane for 2h; Ambient temperature;	95%

: 4163-60-4
β-D-galactose peracetate

: 70191-05-8
2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

Conditions

Conditions	Yield
With acetic acid; hydrazine In N,N-dimethyl-formamide at 60℃; for 0.5h;	100%
With hydrazinium monoacetate In N,N-dimethyl-formamide at 50℃; for 0.75h;	90%
With benzylamine In diethyl ether at 0℃; for 2.5h; Molecular sieve;	86%

: 4163-60-4
β-D-galactose peracetate

: 20183-21-5
1-(β-D-galactopyranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

Conditions

Conditions	Yield
With triethylamine In methanol at 20℃; for 24h; Inert atmosphere;	100%
Multi-step reaction with 2 steps 1: 74 percent / hexamethyldisilazane, chlorotrimethylsilane, tin(IV) chloride 2: 80 percent / NH3 / methanol / Ambient temperature View Scheme

: 4163-60-4
β-D-galactose peracetate

: 16977-78-9, 85193-55-1, 86651-32-3, 86651-40-3
2-bromoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Conditions

Conditions	Yield
	100%

: 4163-60-4
β-D-galactose peracetate

: 3068-32-4
1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 0 - 20℃; for 4h; Inert atmosphere;	99%
With hydrogen bromide; acetic acid In dichloromethane at 0℃; for 1h;
With hydrogen bromide In acetic anhydride; acetic acid at 20℃; for 2h;

: 106-45-6
para-thiocresol

: 4163-60-4
β-D-galactose peracetate

: 28244-94-2, 28244-99-7, 86782-41-4, 131488-65-8
4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	99%
With indium(III) bromide In dichloromethane at 20℃; for 2h; stereoselective reaction;	96%
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 2h;	95%

: 112-55-0
1-dodecylthiol

: 4163-60-4
β-D-galactose peracetate

: 495394-47-3
dodecyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 0 - 20℃;	99%
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 0 - 20℃;	94.8%
With indium(III) bromide In chloroform Reflux;

: 4163-60-4
β-D-galactose peracetate

: 572-09-8, 3068-32-4, 4026-32-8, 6919-96-6, 13242-53-0, 14227-54-4, 14795-18-7, 19186-59-5, 21698-13-5, 29907-26-4, 53369-42-9, 60619-58-1, 61303-35-3, 67337-79-5, 69127-37-3, 70749-15-4, 72002-90-5, 75247-30-2, 75880-74-9, 78418-57-2, 102339-89-9, 102339-90-2, 103530-40-1, 114028-03-4, 114718-45-5, 138514-70-2, 138514-71-3, 19285-38-2
acetobromogalactose

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 0 - 20℃; for 4h; Inert atmosphere;	99%
With hydrogen bromide; acetic acid at 0 - 20℃; for 4h; Inert atmosphere;	99%
With hydrogen bromide; acetic acid for 1h; Inert atmosphere;	89%

: 75-08-1
ethanethiol

: 4163-60-4
β-D-galactose peracetate

: 55722-49-1
ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 3h; Substitution;	98%
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 5h; Inert atmosphere;	98%
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 0.25h;	98%

: 150-76-5
4-methoxy-phenol

: 4163-60-4
β-D-galactose peracetate

: 2872-65-3, 14581-81-8, 17042-40-9, 84380-06-3, 105260-62-6
4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	98%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 4h; Substitution;	92%
With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane	92%

: 91-60-1
2-Naphthalenethiol

: 4163-60-4
β-D-galactose peracetate

: 7464-38-2
2-naphthyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 4h; Substitution;	98%
With tin(IV) chloride In dichloromethane at 20℃; for 4h;	78%

: 75-08-1
ethanethiol

: 4163-60-4
β-D-galactose peracetate

: ethyl 2,3,4-tri-O-acetyl-1-thio-D-galactopyranoside

Conditions

Conditions	Yield
With indium(III) chloride; titanium tetrachloride In acetonitrile at 20℃; for 0.416667h;	98%

: 17242-85-2
5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine

: 4163-60-4
β-D-galactose peracetate

: 1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-5-fluorouracil

Conditions

Conditions	Yield
With poly(4,5-diphenyl-2-vinyloxazolium perchlorate) In acetonitrile for 24h; Vorbrueggen Nucleoside Synthesis; Schlenk technique; Inert atmosphere; Reflux;	98%

: (2-(methylthio)phenyl)methanethiol

: 4163-60-4
β-D-galactose peracetate

: 2-bromobenzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 3h;	97%

: 645-96-5
Benzeneselenol

: 4163-60-4
β-D-galactose peracetate

: 154618-72-1
phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-galactopyranoside

Conditions

Conditions	Yield
With indium(III) bromide In dichloromethane at 20℃; for 2h; stereoselective reaction;	96%
With boron trifluoride diethyl etherate

: 507-09-5
thioacetic acid

: 4163-60-4
β-D-galactose peracetate

: 6806-56-0
2,3,4,6-tetra-O-acetyl-1S-acetyl-1-thio-β-D-galactopyranose

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 30℃; for 5h; Inert atmosphere; stereoselective reaction;	96%
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 24.25h; Inert atmosphere;	89%
With aluminium trichloride In dichloromethane at 50℃; for 2h;	84%

: 4163-60-4
β-D-galactose peracetate

A: 70191-05-8
2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

B: 3947-62-4, 6207-76-7, 10343-06-3, 19235-21-3, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 22554-70-7
2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

Conditions

Conditions	Yield
With ammonia In acetonitrile at 20℃; for 24h; Ammonolysis; Title compound not separated from byproducts;	A n/a B 96%
Stage #1: β-D-galactose peracetate With tributyltin methoxide In tetrahydrofuran for 5h; Heating / reflux; Stage #2: With hydrogenchloride In water
With lipase from Pseudomonas stutzeri In water for 8h; Solvent; Reagent/catalyst; Temperature; Green chemistry; Enzymatic reaction; Overall yield = 90 %; regioselective reaction;

: 4163-60-4
β-D-galactose peracetate

: S-tetraacetyl-β-D-galactosylisothiourea fluorine salt

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; thiourea In dichloromethane at 20℃; for 12h;	96%

: 4163-60-4
β-D-galactose peracetate

: 14227-87-3
2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl chloride

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at 70℃; for 0.166667h; microwave irradiation;	95%
With thionyl chloride; tin(IV) chloride In dichloromethane at 20℃;	91%
With thionyl chloride; zinc(II) chloride; benzene

: 4163-60-4
β-D-galactose peracetate

: 61474-17-7
6-hydroxy-1,2,3,4-tetra-O-acetyl-β-D-galactopyranose

Conditions

Conditions	Yield
octyl-immobilized lipase from Thermomyces lanuginose In phosphate buffer; acetonitrile at 25℃; for 23h; pH=5; Enzyme kinetics;	95%
With immobilized on octyl-agarose; Candida rugosa lipase In phosphate buffer; water; acetonitrile for 48h; pH=5;	43%

: 108-40-7
toluene-3-thiol

: 4163-60-4
β-D-galactose peracetate

: 3-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Conditions

Conditions	Yield
With indium(III) bromide In dichloromethane at 20℃; for 2h; stereoselective reaction;	95%
With tin(IV) chloride In dichloromethane at 20℃; for 4h;	53%

: 146292-90-2
6-azidohexan-1-ol

: 4163-60-4
β-D-galactose peracetate

: 167016-41-3
6-azidohexyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.75h; sonication;	95%

: 140-89-6
potassium ethyl xanthogenate

: 4163-60-4
β-D-galactose peracetate

: 29587-08-4
2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl-aethylxanthat

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In chloroform at -8℃; for 4h; Solvent; Temperature; Reagent/catalyst;	95%

beta-D-Galactose pentaacetate Chemical Properties

IUPAC Name: [(2S,3R,4S,5S,6R)-2,3,5-Triacetyloxy-6-(acetyloxymethyl)oxan-4-yl]acetate
Following is the structure of beta-D-Galactose pentaacetate (CAS NO.4163-60-4):

Molecular Formula: C₁₆H₂₂O₁₁
Molecular Weight: 390.3393
EINECS: 224-008-0
Density:1.3 g/cm³
Flash Point:188.1 °C
Index of Refraction:1.482
Boiling Point:434.8 °C at 760 mmHg
Vapour Pressure:9.23E-08 mmHg at 25°C
Melting point:143-144 °C(lit.)
Storage temp:-20 °C
Solubility of beta-D-Galactose pentaacetate (CAS NO.4163-60-4): methanol: 50 mg/mL, clear
Appearance of beta-D-Galactose pentaacetate (CAS NO.4163-60-4): white fine crystalline powder
Product Categories of beta-D-Galactose pentaacetate (CAS NO.4163-60-4): Sugars, Carbohydrates & Glucosides; Biochemistry; Galactose; O-Substituted Sugars; Sugars
Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
InChI: InChI=1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13+,14+,15-,16-/m1/s1
InChIKey: LPTITAGPBXDDGR-LYYZXLFJSA-N

beta-D-Galactose pentaacetate Toxicity Data With Reference

beta-D-Galactose pentaacetate (CAS NO.4163-60-4) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated.

beta-D-Galactose pentaacetate Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36/37/39-27-26
S24/25:Avoid contact with skin and eyes.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S27:Take off immediately all contaminated clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 1

beta-D-Galactose pentaacetate Specification

beta-D-Galactose pentaacetate , its cas register number is 4163-60-4. It also can be called beta-D-Galactose pentaacetate (VAN) ; and 1,2,3,4,6-Penta-O-acetyl-beta-D-galactopyranose; Penta-O-acetyl-beta-D-galactopyranose . Its classification code is TSCA Flag P [A commenced PMN (Premanufacture Notice) substance].
beta-D-Galactose pentaacetate (CAS NO.4163-60-4) could be stable under normal temperatures and pressures. It should avoid the condition like incompatible materials. It is not compatible with strong oxidizing agents. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide. However, its hazardous polymerization will not occur.

Product Name

beta-D-Galactose pentaacetate

Synthetic route

beta-D-Galactose pentaacetate Chemical Properties

beta-D-Galactose pentaacetate Toxicity Data With Reference

beta-D-Galactose pentaacetate Safety Profile

beta-D-Galactose pentaacetate Specification

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