2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone supplier

Name
2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE
EINECS
CAS No. 13096-62-3
Article Data95
CAS DataBase
Density 1.22 g/cm³
Solubility
Melting Point
Formula C₃₄H₃₄O₆
Boiling Point 677.651 °C at 760 mmHg
Molecular Weight 538.64
Flash Point 283.08 °C
Transport Information
Appearance
Safety
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone;
PSA 63.22000
LogP 5.88480

Synthetic route

: 4291-69-4, 6386-24-9, 6564-72-3, 59531-24-7, 69257-52-9, 78184-89-1, 78609-16-2, 78609-17-3, 78609-18-4, 96553-53-6, 104111-61-7, 131347-08-5, 4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Solvent;	100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h;	100%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h;	100%

: 59531-24-7
2,3,4,6-tetra-O-benzyl-D-glucopyranoside

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
With acetic anhydride; dimethyl sulfoxide at 20℃;	93%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside In dimethyl sulfoxide at 20 - 25℃; for 0.5h; Inert atmosphere; Stage #2: With acetic anhydride at 15 - 25℃; Inert atmosphere;	92%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h;	82%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 105h; Stage #2: With triethylamine In dichloromethane at -78 - 20℃; for 1h;

: 6564-72-3
2,3,4,6-tetra-O-benzyl-D-glucopyranose

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
With acetic anhydride In dimethyl sulfoxide at 20℃;	89%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: With tetrapropylammonium perruthenate In dichloromethane at 20℃; for 2h;	82%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve; Stage #2: tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h;	82%

: 128984-82-7
(2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Amberlite IR 120 H+ In 1,4-dioxane for 3h; Heating;	88%

: 627466-64-2
2,3,4,6-tetra-O-benzoyl-D-glucopyranose

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Oxidation;	85%

: 1-O-allyloxycarbonyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
With palladium diacetate In acetonitrile at 80℃; for 2h;	60%

: phenacyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

A: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B: (3R,4S,6R,7R,8S,9R)-7,8,9-Tris-benzyloxy-6-benzyloxymethyl-3-phenyl-1,5-dioxa-spiro[3.5]nonan-3-ol

Conditions

Conditions	Yield
In benzene for 5h; Ambient temperature; Irradiation;	A 57% B 24%

: 172986-43-5
phenacyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

A: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B: (3R,4S,6R,7R,8S,9R)-7,8,9-Tris-benzyloxy-6-benzyloxymethyl-3-phenyl-1,5-dioxa-spiro[3.5]nonan-3-ol

Conditions

Conditions	Yield
In benzene for 5h; Ambient temperature; Irradiation;	A 56% B 20%

: 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-tert-butyl sulfinothioate

A: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B: 118206-39-6
2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

Conditions

Conditions	Yield
In toluene at 110℃; Inert atmosphere;	A 45% B 45%

: 82598-88-7
2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone

A: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B: 62641-00-3
<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone

Conditions

Conditions	Yield
With magnesium iodide In ethanol at 20℃; for 1h;	A 35% B 5%

: 154127-55-6
2,3,4,6-tetra-O-benzyl-β-1-C-(2-thiazolyl)-D-glucopyranose

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
With 4 A molecular sieve In toluene at 130℃; for 14h; closed vial; Yield given;

: 98-59-9
p-toluenesulfonyl chloride

: (5R,6R,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1-methyl-4-oxa-1,2-diaza-spiro[2.5]octane

A: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B: 1'-methyl-2'-[(Z)-2,3,4,6-tetra-O-benzyl-D-glucopyranosyllidene]toluene-4-sulfohydrazide

Conditions

Conditions	Yield
With pyridine In dichloromethane for 3.5h; Title compound not separated from byproducts;

...Expand

: 3879-79-6, 17791-37-6, 19488-61-0, 53008-63-2, 61330-62-9, 69237-94-1, 69237-95-2, 71526-33-5, 83462-67-3, 84799-77-9, 103421-29-0, 103421-30-3, 139241-42-2
methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: TfOH / H2O 2: DMSO / acetic anhydride View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride; strontium (III) chloride hexahydrate / acetic acid; water / 70 °C 2: caesium carbonate; Iodine monochloride / dichloromethane / 3 h / 0 - 20 °C / Green chemistry View Scheme
Multi-step reaction with 2 steps 1: acetic acid; hydrogenchloride / water / 85 °C 2: acetic anhydride / dimethyl sulfoxide / 22 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid / Reflux 2: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid / water / 2 h / Reflux 2: acetic anhydride / dimethyl sulfoxide / 20 °C View Scheme

: 97-30-3
methyl-alpha-D-glucopyranoside

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; acetic acid / water / 6 h / Reflux 2: acetic anhydride / dimethyl sulfoxide / 16 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: hydrogenchloride; strontium (III) chloride hexahydrate / acetic acid; water / 70 °C 3.1: caesium carbonate; Iodine monochloride / dichloromethane / 3 h / 0 - 20 °C / Green chemistry View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: acetic acid; hydrogenchloride / water / 85 °C 3.1: acetic anhydride / dimethyl sulfoxide / 22 h / 20 °C / Inert atmosphere View Scheme

: 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
D-glucose pentaacetate

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: methanol; sodium methylate / 20 °C 2.2: Amberlite.(R). IR-120 H+ ion exchange 3.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere 3.2: 12 h / 20 °C / Inert atmosphere 4.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C 5.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C View Scheme
Multi-step reaction with 5 steps 1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 0 - 20 °C 2: sodium methylate; methanol 3: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C 4: N-iodo-succinimide; water / acetone 5: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: methanol; sodium methylate / 20 °C
2.2: Amberlite.(R). IR-120 H+ ion exchange
3.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere
3.2: 12 h / 20 °C / Inert atmosphere
4.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C
5.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C
View Scheme

Multi-step reaction with 5 steps
1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 0 - 20 °C
2: sodium methylate; methanol
3: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
4: N-iodo-succinimide; water / acetone
5: acetic anhydride; dimethyl sulfoxide / 20 °C
View Scheme

: 38184-10-0
phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C 2: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C View Scheme

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

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C 3.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C View Scheme

: 13992-16-0, 23661-28-1, 24404-53-3, 28512-68-7, 65236-85-3, 86782-39-0, 108032-93-5, 121524-01-4, 121570-34-1
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: methanol; sodium methylate / 20 °C 1.2: Amberlite.(R). IR-120 H+ ion exchange 2.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 3.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C 4.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C View Scheme

: 6207-45-0, 60478-61-7, 112344-80-6, 126924-14-9, 6207-44-9
2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 70 °C 1.2: 2 h / 20 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C 2.2: -78 - 0 °C View Scheme

: 13992-16-0, 23661-28-1, 24404-53-3, 28512-68-7, 65236-85-3, 86782-39-0, 108032-93-5, 121524-01-4, 121570-34-1
phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium methylate; methanol 2: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C 3: N-iodo-succinimide; water / acetone 4: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme

: 2936-70-1, 5624-48-6, 13992-15-9, 16758-34-2, 28244-97-5, 77481-62-0, 77481-63-1, 105088-17-3, 149495-84-1
phenyl 1-thio-D-glucopyranoside

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C 2: N-iodo-succinimide; water / acetone 3: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme

: 91602-61-8, 38184-10-0, 62774-37-2, 74801-29-9, 116501-52-1, 116501-53-2, 139974-84-8
phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-iodo-succinimide; water / acetone 2: acetic anhydride; dimethyl sulfoxide / 20 °C View Scheme

: 84799-77-9
methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; water; sulfuric acid / 1 h / 110 °C 2: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride; acetic acid / water / 5 h / 100 °C / Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 48 h / 20 °C / Inert atmosphere; Molecular sieve View Scheme

: 97-30-3, 617-04-9, 709-50-2, 1824-94-8, 2152-78-5, 3396-99-4, 6819-48-3, 18469-06-2, 20550-04-3, 22277-65-2, 29411-57-2, 35437-40-2, 35437-43-5, 36191-11-4, 36191-12-5, 39598-79-3, 39598-80-6, 39598-89-5, 51023-63-3, 51223-62-2, 51224-38-5, 51224-39-6, 51224-40-9, 51224-41-0, 51819-81-9, 51819-82-0, 51819-83-1, 56688-81-4, 62279-53-2, 64281-79-4, 64281-80-7, 64912-19-2, 66101-73-3, 78184-90-4, 84368-39-8, 84368-40-1, 84368-41-2, 92142-37-5, 93302-26-2, 103421-28-9, 115794-08-6, 3149-68-6
methyl D-glucopyranoside

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.5 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 20 °C / Inert atmosphere 2.1: acetic acid; water; sulfuric acid / 1 h / 110 °C 3.1: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0.33 h / 55 °C 2: hydrogenchloride / tetrahydrofuran / 0.25 h / 20 °C 3: sodium hydroxide; dihydrogen peroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water / 0.17 h / 65 °C View Scheme

: 100-39-0
benzyl bromide

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.5 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / 20 °C / Inert atmosphere 2.1: acetic acid; water; sulfuric acid / 1 h / 110 °C 3.1: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: hydrogenchloride; strontium (III) chloride hexahydrate / acetic acid; water / 70 °C 3.1: caesium carbonate; Iodine monochloride / dichloromethane / 3 h / 0 - 20 °C / Green chemistry View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: acetic acid; hydrogenchloride / water / 85 °C 3.1: acetic anhydride / dimethyl sulfoxide / 22 h / 20 °C / Inert atmosphere View Scheme

: 72174-24-4, 53269-97-9
(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol

A: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B: 118206-39-6
2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere 2: toluene / 110 °C / Inert atmosphere View Scheme

: 53269-96-8, 116429-58-4, 116429-59-5, 130738-70-4, 141561-28-6
O-ethyl S-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl) dithiocarbonate

A: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B: 118206-39-6
2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium / methanol / 2 h / 20 °C 2: triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere 3: toluene / 110 °C / Inert atmosphere View Scheme

: 100-44-7
benzyl chloride

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0.33 h / 55 °C 2: hydrogenchloride / tetrahydrofuran / 0.25 h / 20 °C 3: sodium hydroxide; dihydrogen peroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water / 0.17 h / 65 °C View Scheme

: 109-72-8, 29786-93-4
n-butyllithium

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 2,3,4,6-tetra-O-benzyl-1-C-butyl-D-glucopyranose

Conditions

Conditions	Yield
at -78℃;	100%
In tetrahydrofuran; toluene at -50℃; for 2h;	72%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 591-51-5
phenyllithium

: 118436-89-8, 118436-90-1
(2,3,4,6-tetra-O-benzyl-1-C-phenyl)-D-glucopyranose

Conditions

Conditions	Yield
at -78℃;	100%
In tetrahydrofuran 1.) -78 deg C, 2 h, 2.) from -78 deg C to room temperature, 2 h;	85.7%
In tetrahydrofuran at -78℃;

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: (3-methylindol-1-yl)magnesium bromide

: (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-1-(3-methyl-indol-1-yl)-hexan-1-one

Conditions

Conditions	Yield
In tetrahydrofuran; toluene at -20℃;	100%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 874357-34-3
(3R,4S,5R,6R)-3,4,5-trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-ethylbenzo[b]thiophen-2-yl-methyl)naphthalen-1-yl]tetrahydropyran-2-ol

Conditions

Conditions	Yield
Stage #1: 2-(4-bromo-naphthalen-2-ylmethyl)-5-ethylbenzo[b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 0.0833333h;	100%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 655237-57-3
((3-bromo-4-fluorobenzyl)oxy)(tert-butyl)dimethylsilane

: 2,3,4,6-tetra-O-benzyl-1-C-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-D-glucopyranose

Conditions

Conditions	Yield
Stage #1: ((3-bromo-4-fluorobenzyl)oxy)(tert-butyl)dimethylsilane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 1h;	100%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 1030825-20-7
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-2-ol

Conditions

Conditions	Yield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 20℃; for 3h;	99%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 372-38-3
1,3,5-trifluorobenzene

: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(2,4,6-trifluorophenyl)tetrahydro-2H-pyran-2-ol

Conditions

Conditions	Yield
Stage #1: 1,3,5-trifluorobenzene With n-butyllithium In diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In diethyl ether at -78℃; for 0.25h; Inert atmosphere; Stage #3: With acetic acid In diethyl ether at -78℃; for 0.166667h; Inert atmosphere;	98%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 76670-93-4
2,3,4,6-tetra-O-benzyl-D-gluconamide

Conditions

Conditions	Yield
With ammonia In methanol at 0℃; for 2h;	97%
With ammonia In methanol	96%
With ammonia In methanol at 0℃; for 3h;	96%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 590-15-8
trans-2-propenyl bromide

: (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-prop-1-ynyl-tetrahydro-pyran-2-ol

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	97%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 57-55-6
propylene glycol

: 77855-88-0, 77881-86-8
1,2-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-1,2-propanediol

Conditions

Conditions	Yield
With sulfuric acid In benzene for 24h; Heating;	96.2%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

O-(tert-butyl)hydroxylamine hydrochloride: O-(tert-butyl)hydroxylamine hydrochloride

: 1N-tert-butoxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

Conditions

Conditions	Yield
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination;	96%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 62641-00-3
<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone

Conditions

Conditions	Yield
With sodium hydride; acetophenone In tetrahydrofuran 1.) 45 deg C, 30 min, 2.) 25 deg C, 5 min.;	95%
With sodium methylate In methanol for 0.5h; Ambient temperature;	40 mg

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 756-79-6
dimethyl methane phosphonate

: 140926-87-0
3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 1h;	95%
With n-butyllithium	92%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.333333h; Metallation; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -70 - -40℃; for 1h; Addition;	91%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78 - 0℃; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water; ethyl acetate cooling with ice;

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 53913-96-5
tert-butyl 2-(bromomethyl)acrylate

: 2-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-ylmethyl)-acrylic acid tert-butyl ester

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃;	95%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 593-56-6
N-methoxylamine hydrochloride

: 1N-methoxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

Conditions

Conditions	Yield
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination;	95%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 141-78-6
ethyl acetate

: 132470-52-1
2-deoxy-4,5,6,8-tetra-O-benzyl-α-D-gluco-3,7-pyranoso-3-octulosonate

Conditions

Conditions	Yield
With lithium hexamethyldisilazane	95%
Stage #1: ethyl acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -60℃; for 0.25h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -60 - 20℃; for 1h; Further stages.;	66%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 6921-34-2
benzylmagnesium chloride

: 389121-73-7
1-C-benzyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Conditions

Conditions	Yield
	95%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 1589-82-8
phenylmagnesium bromide

: 389121-73-7
1-C-benzyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78 - -40℃; for 2h;	95%

: 109-72-8, 29786-93-4
n-butyllithium

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 292149-85-0
2,3,4,6-tetra-O-benzyl-1-C-n-butyl-α-D-glucopyranose

Conditions

Conditions	Yield
Stage #1: n-butyllithium; (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: With water In tetrahydrofuran; hexane Further stages.;	95%
In tetrahydrofuran; hexane at -78℃; for 0.5h; diastereoselective reaction;	92%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 106-95-6
allyl bromide

: (3R,4S,5R,6R)-2,2-diallyl-3,4,5-tris(benzyloxy)-6-(benzyloxy)methyltetrahydropyran

Conditions

Conditions	Yield
With chloro-trimethyl-silane; zinc In tetrahydrofuran at 20℃; for 4h; Barbier Coupling Reaction;	95%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 75-09-2
dichloromethane

: 140658-50-0
2,3,4,6-Tetra-O-benzyl-1-C-(dichloromethyl)-α-D-glucopyranose

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -75 - -70℃; for 1h;	94%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

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

: 261713-59-1
2,3,4,6-tetra-O-benzyl-5',5'-dimethylspiro[1,5-anhydro-D-glucitol-1,2'-[1,3]dioxane]

Conditions

Conditions	Yield
With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate In toluene at 20℃; for 1h;	94%
With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate In toluene at 20℃; for 2h; Cycloaddition;	94%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 917-54-4
methyllithium

: 137344-41-3
3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranose

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78℃; for 0.5h; diastereoselective reaction;	94%
In tetrahydrofuran; diethyl ether at -78℃; for 1h;	83%
In tetrahydrofuran at -78℃; for 0.166667h;	67%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Cp2TiMe2: Cp2TiMe2

: 133697-34-4, 97321-70-5
2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

Conditions

Conditions	Yield
In toluene	94%
In toluene at 65 - 70℃; for 14h;

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 89160-10-1
methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside

: (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylethynyl)-tetrahydro-pyran-2-ol

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -50℃;	93%
With n-butyllithium In tetrahydrofuran at -50℃; for 1h;	92%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 622-33-3
N-benzyloxyamine

: 270062-18-5
1N-benzyloxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

Conditions

Conditions	Yield
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination;	93%
Stage #1: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; N-benzyloxyamine In dichloromethane at 20℃; for 0.5h; Stage #2: With trimethylaluminum In hexane; dichloromethane at 20℃; for 1h; Further stages.;	93%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 3332-29-4
O-ethylhydroxylamine hydrochloride

: 1N-ethoxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

Conditions

Conditions	Yield
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination;	93%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 120363-13-5
tert-butyl 4-iodobenzoate

: 1-C-(4-tert-butoxycarbonylphenyl)-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Conditions

Conditions	Yield
With n-butyllithium; 2,4,6-triisopropyl-1-bromobenzene In tetrahydrofuran at -78℃; for 1h; Reagent/catalyst; Barbier Coupling Reaction; Inert atmosphere; stereoselective reaction;	93%
Stage #1: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; tert-butyl 4-iodobenzoate With 2,4,6-triisopropylphenyl lithium In tetrahydrofuran at -78℃; Stage #2: With ammonium chloride In water	93%

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone Specification

The D-Gluconic acid,2,3,4,6-tetrakis-O-(phenylmethyl)-, d-lactone, with the CAS registry number of 13096-62-3, is also known as 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone. It belongs to the product category of Pharmaceutical Intermediates. Its molecular formula is C₃₄H₃₄O₆ and molecular weight is 538.63016. What's more, its systematic name is (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one.

Physical properties about the D-Gluconic acid,2,3,4,6-tetrakis-O-(phenylmethyl)-, d-lactone are: (1)ACD/LogP: 6.11; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 8; (4)ACD/LogD (pH 7.4): 8; (5)ACD/BCF (pH 5.5): 448591; (6)ACD/BCF (pH 7.4): 448591; (7)ACD/KOC (pH 5.5): 386515; (8)ACD/KOC (pH 7.4): 386515; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 13; (12)Polar Surface Area: 63.22 Å²; (13)Index of Refraction: 1.614; (14)Molar Refractivity: 153.888 cm³; (15)Molar Volume: 441.363 cm³; (16)Surface Tension: 53.757 dyne/cm; (17)Density: 1.22 g/cm³; (18)Flash Point: 283.08 °C; (19)Enthalpy of Vaporization: 99.474 kJ/mol; (20)Boiling Point: 677.651 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C5O[C@H](COCc1ccccc1)[C@@H](OCc2ccccc2)[C@H](OCc3ccccc3)[C@H]5OCc4ccccc4
(2) InChI: InChI=1/C34H34O6/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-33H,21-25H2/t30-,31-,32+,33-/m1/s1
(3) InChIKey: BUBVLQDEIIUIQG-NXVJRICRBN

Product Name

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Synthetic route

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone Specification

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