572-09-8

Basic information

• Product Name: 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
• Synonyms: acetobromo-a-d-glucose;alpha-d-glucopyranosylbromide,tetraacetate;α-D-Glucopyranosylbromide,tetraacetate;TETRA-O-ACETYL-A-D-GLUCOPYRANOSYL BROMIDE;TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE;ALPHA-ACETOBROMO-D-GLUCOSE;ACETOBROMO-D-GLUCOSE;ACETOBROMOGLUCOSE
• CAS NO: 572-09-8
• Molecular Formula: C14H19BrO9
• Molecular Weight: 411.2
• EINECS: 209-339-0
• Product Categories: Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Biochemistry;Glucose;Halogenosugars;Sugars;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives;Carbohydrates
• Mol File: 572-09-8.mol
• Article Data: 384

Chemical Properties

• Melting Point: 86-89 °C
• Boiling Point: 412 °C at 760 mmHg
• Flash Point: 203 °C
• Appearance: White to beige/Powder
• Density: 1.49 g/cm³
• Refractive Index: 1.541
• Storage Temp.: −20°C
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,60
• BRN: 96669
• CAS DataBase Reference: 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide(572-09-8)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide(572-09-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• F: 8-10-21
• Hazardous Substances Data: 572-09-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 572-09-8 differently. You can refer to the following data:
1. An Intermediate in synthesis of ∫-glucosides
2. Acetobromo-α-D-glucose acts as an intermediate in the preparation of beta-glucosides. It is also used as a possible poly(ethylene terephthalate) surface modification reagent to enhance its blood compatibility.

Purification Methods

If nicely crystalline, recrystallise it from Et2O/pentane or pet ether (b 40-60o). Alternatively dissolve it in diisopropyl ether (dried over CaCl2 for 24hours, then over P2O5 for 24hours) by shaking and warming (for as short a period as possible), and filter warm. Cool to ca 45o, then slowly to room temperature and finally at 5o for more than 2hours. Collect the solid, wash it with cold dry diisopropyl ether and dry it in a vacuum over Ca(OH)2 and NaOH. Store it dry in a desiccator in the dark. Solutions can be stabilised with 2% CaCO3. [Redemann & Niemann Org Synth 65 236 1987, Coll Vol III 11 1955, Beilstein 17/6 V 368.]

InChI:InChI=1/C8H13BrO7/c1-4(12)15-6(3-11)8(16-9)7(14)5(13)2-10/h3,5-8,10,13-14H,2H2,1H3/t5-,6+,7-,8-/m1/s1

Synthetic route

β-D-glucose pentaacetate (604-69-3) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With hydrogen bromide In dichloromethane Ambient temperature;	100%
With hydrogen bromide; acetic acid at 20℃; for 4h;	100%
With hydrogen bromide at 20℃; for 1.16667h;	100%

D-glucose pentaacetate (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) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With hydrogen bromide; acetic acid at 20℃; Product distribution / selectivity;	100%
With hydrogen bromide; acetic acid at 20℃; for 2h;	100%
With hydrogen bromide; acetic acid In dichloromethane at 20℃; for 3h;	100%

α-D-glucopyranose peracetylate (604-68-2) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With hydrogen bromide; acetic acid	100%
Stage #1: α-D-glucopyranose peracetylate With hydrogen bromide; acetic acid Stage #2: at 0 - 20℃; for 2h;	98%
With acetic anhydride; phosphorus tribromide In water at 0℃; for 1h;	95%

alpha-D-glucopyranose (492-62-6) + Acetyl bromide (506-96-7) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With perchloric acid In methanol at 20℃; for 2h;	99%

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2872-65-3, 14581-81-8, 17042-40-9, 84380-06-3, 105260-62-6) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With Acetyl bromide; zinc dibromide In dichloromethane at 22℃; for 24h;	97%

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With hydrogen bromide; acetic acid In dichloromethane at 0℃; for 8h;	96%
With pyridine; (PhO)3P*Br2 In dichloromethane for 0.0833333h;	89%
With hydrogen bromide; acetic anhydride In dichloromethane at 20℃; for 4h;	85%

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
Stage #1: D-Glucose With Acetyl bromide In methanol Stage #2: acetic anhydride With acetic acid	95%
Stage #1: D-Glucose; acetic anhydride With perchloric acid; acetic acid at 20℃; for 0.5h; Stage #2: With Acetyl bromide In methanol for 2h;	90%
Stage #1: D-Glucose; acetic anhydride With sodium acetate at 100℃; for 5h; Stage #2: With hydrogen bromide; acetic acid In dichloromethane at 20℃; for 6h;	90%

alpha-D-glucopyranose (492-62-6) + acetic anhydride (108-24-7) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
Stage #1: alpha-D-glucopyranose; acetic anhydride With perchloric acid at 30 - 40℃; for 1h; Stage #2: With phosphorus; bromine at 20℃; Cooling with ice; Stage #3: With water at 20℃; for 3.16667h;	90%
With hydrogen bromide; acetic acid at 20℃; for 11h;	89%
With hydrogen bromide; acetic acid at 20℃; for 11h;	85.88%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With hydrogen bromide In dichloromethane; acetic acid at 20℃; for 6h;	86%
With hydrogen bromide In acetic acid

4-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (160227-12-3) → 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide (4753-07-5) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4)

Conditions	Yield
With Acetyl bromide; zinc dibromide In dichloromethane at 22℃; Yields of byproduct given;	A 82% B n/a C n/a

ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl disulfide (231607-35-5) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With 4 A molecular sieve; iodine(I) bromide In dichloromethane at 20℃;	82%
With iodine(I) bromide In dichloromethane at 20℃; for 0.5h;	82%

1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (100432-86-8) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane Irradiation;	78%
With N-Bromosuccinimide In tetrachloromethane Product distribution; Irradiation; other glucopyranoside, other reagent, other solvent;

C20H23NO11 → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With copper(ll) bromide In dichloromethane at 20℃; Molecular sieve; Inert atmosphere;	78%

C20H28O9S → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With iodine(I) bromide In dichloromethane; toluene at 20℃; for 1h; Molecular sieve; Inert atmosphere;	78%

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3) + 1-bromo-N,N,2-trimethyl-1-propen-1-amine (73630-93-0) → N,N,2-trimethylpropionamide (21678-37-5) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
In chloroform for 6h; Product distribution; Ambient temperature;	A n/a B 77%

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester (604-70-6) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With acyl bromide; zinc dibromide In dichloromethane for 12h; Heating;	75%
With trimethylsilyl bromide; zinc dibromide In dichloromethane for 24h; Ambient temperature;	47%

methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4860-85-9) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With acyl bromide; zinc dibromide In dichloromethane for 12h; Heating;	71%

1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (100432-86-8) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With Bromotrichloromethane In tetrachloromethane Irradiation;	A 30% B 65%

D-Glucose (2280-44-6) + Acetyl bromide (506-96-7) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
Stage #1: D-Glucose With perchloric acid; acetic anhydride at 30 - 40℃; for 0.5h; Stage #2: Acetyl bromide With water at 20℃; for 2h;	57.5%
With aluminum oxide In acetonitrile at 20℃; for 4h;	20%
In acetic acid for 2h; Ambient temperature;
With sulfuric acid

n-hexyl caproate (6378-65-0) + β-D-glucose pentaacetate (604-69-3) → hexanoic acid (142-62-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With bromine at 20℃; Irradiation; Green chemistry;	A n/a B 57%

n-decyl acetate (112-17-4) + β-D-glucose pentaacetate (604-69-3) → 1-bromo dodecane (112-29-8) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With bromine at 20℃; Irradiation; Green chemistry;	A n/a B 57%

1,2,3,4,6-penta-O-acetyl-D-glucose → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With hydrogen bromide; acetic acid at 20℃; for 2h;	53%

β-D-glucose pentaacetate (604-69-3) → 1,3,4,6-tetra-O-acetyl 2-bromo-2-deoxy-α-D-glucopyranose (29585-29-3) + 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With bromine In 2,2,4-trimethylpentane; dichloromethane at 20℃; for 7h; Irradiation; Green chemistry;	A 7% B 15% C 22%

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-1-C-sulfonamide (1138026-28-4) → 2,3,4,6-tetra-O-acetyl-1-C-bromo-β-D-glucopyranosyl-1-C-sulfonamide + 2,3,4,6-tetra-O-acetyl-5-C-bromo-β-D-glucopyranosyl-1-C-sulfonamide + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With bromine; potassium carbonate In α,α,α-trifluorotoluene for 4h; Reflux; Heat lamp;	A 12% B 12% C 19%

β-D-glucose pentaacetate (604-69-3) → 1,2,3,4,6-Penta-O-acetyl-5-bromo-β-D-glucopyranose (69534-61-8) + 2,3,4,6-tetra-O-acetyl-1-bromo-D-glucopyranosyl bromide (75868-36-9) + 2,3,4,6-tetra-O-acetyl-5-bromo-β-D-glucopyranosyl bromide (75860-51-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With bromine In tetrachloromethane for 3h; Heating; Irradiation;	A n/a B n/a C 13% D 0.06 g
With bromine In tetrachloromethane for 3h; Heating; Irradiation; Yield given;	A n/a B n/a C 13% D 0.06 g
With bromine In tetrachloromethane for 3h; Heating; Irradiation; Yields of byproduct given;	A n/a B n/a C 13% D 0.06 g

β-D-glucose pentaacetate (604-69-3) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) + α-D-glucopyranose peracetylate (604-68-2)

Conditions	Yield
With bromine In ethyl acetate at 20℃; for 19h; Irradiation; Darkness; Green chemistry;	A 8% B n/a

D-glucose (50-99-7) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With Acetyl bromide; acetic acid
Multi-step reaction with 2 steps 1.1: pyridine / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 6 h / 20 °C / Inert atmosphere 2.1: hydrogen bromide; acetic acid / dichloromethane / 1 h / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: pyridine / 6 h / 0 °C 2: acetic acid; hydrogen bromide / dichloromethane / 2 h View Scheme

D-glucose (50-99-7) + acetic anhydride (108-24-7) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With perchloric acid anschl. mit Phosphor, Brom und H2O;
With pyridine; hydrogen bromide; acetic acid Yield given; Multistep reaction;
Stage #1: D-glucose; acetic anhydride With iodine at 20℃; for 1h; Stage #2: With hydrogen bromide; acetic acid
Stage #1: D-glucose; acetic anhydride With perchloric acid In water at 40℃; for 1h; Stage #2: With phosphorus; bromine In water at 0 - 20℃; for 4h;

sodium chloride * 2 d-glucose * H2O (77938-63-7) + acetic anhydride (108-24-7) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With sulfuric acid anschl. Behandeln des von der gebildeten Essigsaeure befreiten Rktprod. mit HBr;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1)

Conditions	Yield
With tetramethylguanidinum azide In nitromethane at 25℃; for 2.5h;	100%
With sodium azide In N,N-dimethyl-formamide for 48h; Inert atmosphere;	100%
With N,N,N',N'-tetramethylguanidinium azide In dichloromethane for 2h; Ambient temperature; other glycosyl halides;	99%

lead(II) thiocyanate (592-87-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (14152-97-7)

Conditions	Yield
In benzene for 6h; Heating;	100%
In 5,5-dimethyl-1,3-cyclohexadiene at 130 - 140℃; for 0.416667h; Microwave irradiation;	89.66%
In toluene for 4h; Reflux;	89%

thiourea (17356-08-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide (40591-65-9)

Conditions	Yield
In acetone at 60℃; Inert atmosphere; Reflux;	100%
In acetone for 0.5h; Heating;	95%
In acetone for 0.05h; microwave irradiation;	90%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 3,4,6-tri-O-acetyl-1,2-O-vinylidene-α-D-glucopyranose (165053-19-0)

Conditions	Yield
With silver perchlorate; N-ethyl-N,N-diisopropylamine In benzene at 20℃; for 1h; Molecular sieve; Inert atmosphere; Darkness;	100%
With N-ethyl-N,N-diisopropylamine; silver(l) oxide In benzene for 6h; Heating;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) + 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecanoic acid (4-mercapto-phenyl)-methyl-amide (724733-04-4) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecanoyl)-methyl-amino]-phenylsulfanyl}-tetrahydro-pyran-3-yl ester

Conditions	Yield
With sodium carbonate In water; ethyl acetate at 20℃; for 2h;	100%

CDP-Star enol ether phenol + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → glucon-Star enol ether tetraacetate

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide; phase transfer catalyst In dichloromethane at 20℃; for 0.5h;	100%

2-Nitrobenzyl alcohol (612-25-9) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-nitrobenzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (34546-55-9)

Conditions	Yield
With iodine; silver carbonate In dichloromethane at 20℃; for 16h; Molecular sieve; Inert atmosphere;	100%
With iodine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 4h; Molecular sieve; Inert atmosphere;	91%

C22H24N2O6 + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → C36H42N2O15

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃;	100%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3)

Conditions	Yield
With water; silver carbonate In acetone for 0.5h;	99%
With N-methylacridinium iodide; sodium cyanoborohydride In N,N-dimethyl-formamide for 1h; Reagent/catalyst; Solvent; UV-irradiation;	55.8%
With acetone; silver carbonate

ursolic acid (77-52-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-hydroxyurs-12-en-28-oate (16684-20-1)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In dichloromethane; water for 8h; Heating;	99%
With Aliquat 336; potassium carbonate In dichloromethane; water for 48h; Ambient temperature;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	90%

benzoic acid (65-85-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → O2,O3,O4,O6-Tetraacetyl-O1-benzoyl-β-D-glucopyranose (38430-69-2)

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Reagent/catalyst; Molecular sieve;	99%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Molecular sieve; Inert atmosphere;	84%
With Amberlyst A-26 hydroxide form 1.) hexane, 2.) benzene, reflux, 12 h;	65%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) + naphthalene-2-carboxylate (93-09-4) → 1-O-(2-naphthoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve;	99%
With Aliquat 336; potassium carbonate In dichloromethane; water Ambient temperature;	96%

sodium N,N-diethyldithiocarbamate (148-18-5) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) N,N-diethyldithiocarbamate

Conditions	Yield
In acetone for 1h; Reflux;	99%
In acetonitrile at 25℃; for 1h;	63%

2-thioxo-3H-1,3-benzothiazole (149-30-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosylmercapto)1,3-benzothiazole (6067-32-9, 6426-38-6)

Conditions	Yield
With potassium hydroxide In acetonitrile at 20℃; for 1h;	99%

4-(pyridin-2'-yl)thiazole-2(3H)-thione sodium salt (1095998-03-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 4-(pyridine-2-yl)-thiazole-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (1095998-22-3)

Conditions	Yield
In acetonitrile at 20℃; for 8h; Inert atmosphere;	99%

6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside (74247-81-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → methyl 6-O-tert-butyldimethylsilyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-mannopyranoside (1330004-16-4)

Conditions	Yield
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 23℃; for 16h; Kinetics; Mechanism; Concentration; Reagent/catalyst; Koenigs-Knorr synthesis; Inert atmosphere; regioselective reaction;	99%
With [2-(1-methyl-1H-imidazol-2-yl)phenyl]boronic acid; silver(l) oxide In acetonitrile at 30℃; for 24h; Reagent/catalyst; Koenigs-Knorr Glycosidation; Inert atmosphere; regioselective reaction;	98%

6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-galactopyranoside (181480-80-8) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → methyl 6-O-tert-butyldimethylsilyl-3-O-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-galactopyranoside (1330004-23-3)

Conditions	Yield
With [2-(1-methyl-1H-imidazol-2-yl)phenyl]boronic acid; silver(l) oxide In acetonitrile at 30℃; for 24h; Koenigs-Knorr Glycosidation; Inert atmosphere; regioselective reaction;	99%
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 23℃; for 16h; Koenigs-Knorr synthesis; Inert atmosphere; regioselective reaction;	74%
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 23℃; for 16h; Reagent/catalyst; regioselective reaction;	74%

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → methyl 3-O-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-mannopyranoside

Conditions	Yield
Stage #1: (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 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; Reagent/catalyst; Koenigs-Knorr Glycosidation; stereoselective reaction;	99%

m-bromobenzoic acid (585-76-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-O-(3-bromobenzoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve;	99%

3-methylbutyric acid (503-74-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-O-(3-methylbutanoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve;	99%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) + cyclopropanecarboxylic acid (1759-53-1) → 1-O-(cyclopropanecarbonyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve;	99%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) + potassium thioacetate (10387-40-3) → O2,O3,O4,O6,S-Pentaacetyl-1-thio-β-D-glucopyranose (6806-56-0, 13639-50-4, 51898-27-2, 62860-10-0, 63783-77-7, 92217-67-9, 92217-68-0, 130796-15-5)

Conditions	Yield
for 2h; Neat (no solvent); Ball milling;	98%
In acetone at 20℃; for 8h;	88%
In acetone at 20℃;	86%

allyl alcohol (107-18-6) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester (10343-15-4, 39698-55-0, 54400-76-9, 78730-32-2, 119111-31-8, 119111-32-9)

Conditions	Yield
With copper(II) sulfate; mercury dibromide; mercury(II) oxide In chloroform at 0 - 20℃; for 10h;	98%
With indium(III) chloride; 4 A molecular sieve In dichloromethane at 0 - 3℃; for 72h;	86%
With metal carbonates In neat (no solvent) for 2.5h; Milling;	82%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-deoxy-D-glucose tetraacetate (13137-69-4)

Conditions	Yield
With -butyl vinyl ether	98%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; for 1h;	97%
With 2,2'-azobis(isobutyronitrile); phenylsilane for 1.16667h; Heating;	90%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate (439-03-2, 439-04-3, 439-05-4, 2823-44-1, 2823-46-3, 3934-29-0, 4163-44-4, 4163-45-5, 20409-31-8, 23235-96-3, 51897-75-7, 51897-76-8, 51897-77-9, 57573-38-3, 62561-28-8, 126641-47-2)

Conditions	Yield
With silver fluoride In acetonitrile at 20℃; Inert atmosphere; Darkness;	98%
With triethylamine tris(hydrogen fluoride) In tetrachloromethane for 2h; Heating;	83%
With (trifluoromethyl)zinc chloride; 3 A molecular sieve In dichloromethane for 12h; Ambient temperature;	83%
With potassium hydrogen bifluoride In acetonitrile for 24h; Heating;	70%
With silver fluoride; acetonitrile

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 3,4,6-Tri-O-acetyl-1,2-O-<1-(exo-1,2:3,4-di-O-isopropylidene-α-D-galacatopyranose-6-yl)ethylidene>-α-D-glucopyranose (66964-24-7)

Conditions	Yield
With silver imidazolate; mercury dichloride In dichloromethane for 24h; 3 Angstroem molecular sieves;	98%
With 4 A molecular sieve; tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; under 6000480 Torr; for 20h; Yield given;

Upstream product

• 108-24-7 acetic anhydride 
• 604-69-3 β-D-glucose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 4860-85-9 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 160227-12-3 4-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 50-99-7 D-glucose 
• 492-61-5 β-D-glucose 
• 2280-44-6 D-Glucose 
• 64-19-7 acetic acid 
• 77938-63-7 sodium chloride * 2 d-glucose * H₂O 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 220041-69-0 phenyl-[O²,O³,O⁴-triacetyl-O⁶-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside] 
• 121159-95-3 benzyl-[O²,O³-dibenzyl-O⁶-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside] 
• 21133-53-9 glucofranguline A 
• 70144-59-1 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside 
• 69895-14-3 methyl (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-β-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 485388-48-5 3,4-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzaldehyde 
• 4613-78-9 β-D-gentiobiose octaacetate 
• 114202-82-3 2-(tetra-O-acetyl-β-D-glucopyranosylmercapto)-benzoic acid methylamide 
• 115210-99-6 2-acetoxy-5-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzoic acid ethyl ester 
• 34020-54-7 tetra-O-acetyl-1-phenyl-3,7-anhydro-1,2-dideoxy-D-gulo-oct-1-initol 
• 42344-69-4 2-methoxy-5-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 116865-53-3 2,6-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzoic acid methyl ester 
• 115485-94-4 2-acetoxy-6-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzoic acid methyl ester 
• 51433-06-8 1-(2,5-dimethylphenyl)-β-D-glucopyranose 

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