1,6-Anhydro-beta-d-mannopyranose supplier

Name
1,6-Anhydro-beta-d-mannopyranose
EINECS 207-855-0
CAS No. 14168-65-1
Article Data26
CAS DataBase
Density 1.689 g/cm³
Solubility
Melting Point 182-184 °C
Formula C₆H₁₀O₅
Boiling Point 383.754 °C at 760 mmHg
Molecular Weight 162.142
Flash Point 185.888 °C
Transport Information
Appearance White crystalline solid
Safety 26-36
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Mannopyranose,1,6-anhydro-, b-D-(6CI,8CI);1,6-Anhydro-D-mannose;1,6-Anhydro-b-D-mannopyranose;1,6-Anhydromannose;Mannosan;NSC 226600;
PSA 79.15000
LogP -2.17580

Synthetic route

: 530-26-7
D-Mannose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With p-toluenesulfonyl chloride In pyridine for 4h; Ambient temperature;	80%
With pyridine; p-toluenesulfonyl chloride at 20℃; for 21h; Inert atmosphere;	48.4%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide	20%

: 6619-07-4, 26391-80-0, 121363-57-3, 121363-64-2, 121363-65-3, 121363-70-0
6-O-p-toluenesulfonyl-D-mannopyranose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
NaOH In pyridine; sodium hydroxide for 1h; Ambient temperature;	77%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol Ambient temperature;
With sodium hydride In N,N-dimethyl-formamide for 15h; Ambient temperature;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.5h; Ambient temperature;

: 20888-02-2
1,6-anhydro-2,3,4-tri-O-benzyl-β-D-mannopyranose

A: 104477-48-7
1,6-anhydro-3-O-benzoyl-β-D-mannopyranose

B: 14168-65-1
mannosan

Conditions

Conditions	Yield
palladium on activated charcoal In isopropyl alcohol for 4h; Heating;	A 40% B n/a
With isopropyl alcohol; palladium on activated charcoal for 4h; Heating;	A 40% B n/a

: 13242-48-3
2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With methanol; barium methoxide

: 3458-28-4
D-Mannose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; benzene In N,N-dimethyl-formamide

: 102794-49-0
(1R,2S,6S,7R,8R)-7-Allyloxy-4-vinyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With sodium acetate; palladium dichloride In acetic acid at 20℃; for 24h;

: 14440-51-8
1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In methanol for 30h; Heating;

: 7664-93-9
sulfuric acid

: 3868-04-0
1,6:3,4-dianhydro-β-D-altropyranose

: 14168-65-1
mannosan

O2,O3-isopropyliden-1,6-anhydro-β-D-mannopyranose: O2,O3-isopropyliden-1,6-anhydro-β-D-mannopyranose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With sulfuric acid

: 3458-28-4
D-Mannose

aqueous sulfuric acid (0.2n): aqueous sulfuric acid (0.2n)

: 14168-65-1
mannosan

: 530-26-7
D-Mannose

: 98-59-9
p-toluenesulfonyl chloride

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Stage #1: D-Mannose; p-toluenesulfonyl chloride Tosylation; Stage #2: With sodium hydroxide In water Cyclization; Further stages.;

: 71856-30-9
dianhydroaltrose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Stage #1: dianhydroaltrose With boron trifluoride diethyl etherate Stage #2: With sodium methylate In methanol

: 1,6-anhydro-2-O-benzoyl-β-D-mannopyranoside

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With sodium methylate In methanol

: 5334-19-0
1,6-anhydro-2,3,4-tri-O-benzoyl-β-D-mannopyranose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With sodium methylate In methanol

: 126354-67-4
2,3-isopropylidenedioxy-D-mannono-γ-lactone

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 61 percent / pyridine / 10 h / Ambient temperature 2: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 3: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 4: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 5: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme
Multi-step reaction with 6 steps 1: 61 percent / pyridine / 10 h / Ambient temperature 2: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 3: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 4: 35 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 5: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h 6: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme

Yield

Multi-step reaction with 5 steps
1: 61 percent / pyridine / 10 h / Ambient temperature
2: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature
3: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C
4: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature
5: pyridinium p-toluenesulfonate / methanol / 30 h / Heating
View Scheme

Multi-step reaction with 6 steps
1: 61 percent / pyridine / 10 h / Ambient temperature
2: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature
3: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C
4: 35 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature
5: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h
6: pyridinium p-toluenesulfonate / methanol / 30 h / Heating
View Scheme

: 150161-01-6
2,3-O-Isopropylidene-4-O-t-butyldimethylsilyl-1,6-anhydro-β-D-mannopyranose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h 2: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme

: 150160-98-8
2,3-O-Isopropylidene-6-O-(p-tolylsulfonyl)-D-mannono-1,4-lactone

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 2: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 3: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 4: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 2: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 3: 35 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 4: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h 5: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme

: 2,3-O-Isopropylidene-5-O-tert-butyldimethylsilyl-6-O-(p-tolylsulfonyl)-D-mannofuranose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 2: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 35 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 2: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h 3: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme

: 150160-99-9
2,3-O-Isopropylidene-5-O-tert-butyldimethylsilyl-6-O-(p-tolylsulfonyl)-D-mannono-1,4-lactone

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 2: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 3: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 2: 35 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 3: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h 4: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme

: 14131-84-1
2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 80 percent / Collins' reagent / CH2Cl2 / 0.5 h / Ambient temperature 2: gl. AcOH, water / 4 h / 60 °C 3: 61 percent / pyridine / 10 h / Ambient temperature 4: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 5: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 6: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 7: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme
Multi-step reaction with 8 steps 1: 80 percent / Collins' reagent / CH2Cl2 / 0.5 h / Ambient temperature 2: gl. AcOH, water / 4 h / 60 °C 3: 61 percent / pyridine / 10 h / Ambient temperature 4: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 5: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 6: 35 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 7: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h 8: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme

Yield

Multi-step reaction with 7 steps
1: 80 percent / Collins' reagent / CH2Cl2 / 0.5 h / Ambient temperature
2: gl. AcOH, water / 4 h / 60 °C
3: 61 percent / pyridine / 10 h / Ambient temperature
4: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature
5: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C
6: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature
7: pyridinium p-toluenesulfonate / methanol / 30 h / Heating
View Scheme

Multi-step reaction with 8 steps
1: 80 percent / Collins' reagent / CH2Cl2 / 0.5 h / Ambient temperature
2: gl. AcOH, water / 4 h / 60 °C
3: 61 percent / pyridine / 10 h / Ambient temperature
4: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature
5: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C
6: 35 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature
7: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h
8: pyridinium p-toluenesulfonate / methanol / 30 h / Heating
View Scheme

: 7306-64-1, 14440-56-3, 23262-80-8, 27108-15-2, 49561-21-9, 67642-42-6
2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: gl. AcOH, water / 4 h / 60 °C 2: 61 percent / pyridine / 10 h / Ambient temperature 3: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 4: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 5: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 6: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme
Multi-step reaction with 7 steps 1: gl. AcOH, water / 4 h / 60 °C 2: 61 percent / pyridine / 10 h / Ambient temperature 3: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 4: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C 5: 35 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature 6: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h 7: pyridinium p-toluenesulfonate / methanol / 30 h / Heating View Scheme

Yield

Multi-step reaction with 6 steps
1: gl. AcOH, water / 4 h / 60 °C
2: 61 percent / pyridine / 10 h / Ambient temperature
3: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature
4: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C
5: 12 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature
6: pyridinium p-toluenesulfonate / methanol / 30 h / Heating
View Scheme

Multi-step reaction with 7 steps
1: gl. AcOH, water / 4 h / 60 °C
2: 61 percent / pyridine / 10 h / Ambient temperature
3: 98 percent / imidazole / dimethylformamide / 10 h / Ambient temperature
4: 90 percent / iBu2AlH / hexane; toluene / 4 h / -78 °C
5: 35 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature
6: 70 percent / Bu4NF / tetrahydrofuran / 0.17 h
7: pyridinium p-toluenesulfonate / methanol / 30 h / Heating
View Scheme

: 3458-28-4
D-Mannose

A: 31880-33-8
1,6-Anhydro-β-D-mannohexofuranose

B: 14168-65-1
mannosan

Conditions

Conditions	Yield
With water In sulfolane at 220℃; for 0.05h; Microwave irradiation;	A 14.7 %Chromat. B 63.9 %Chromat.

: 4097-91-0
methyl α-D-mannofuranoside

A: 31880-33-8
1,6-Anhydro-β-D-mannohexofuranose

B: 14168-65-1
mannosan

Conditions

Conditions	Yield
In sulfolane at 240℃; for 0.05h; Microwave irradiation;	A 57.1 %Chromat. B 5.8 %Chromat.
With water In sulfolane at 240℃; for 0.05h; Microwave irradiation;	A 12.5 %Chromat. B 48.1 %Chromat.

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With water In sulfolane at 280℃; for 0.05h; Microwave irradiation;	79.8 %Chromat.

: 6-O-toluenesulfonyl-β-D-mannopyranose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
With sodium hydroxide at 0 - 20℃; Inert atmosphere;

: 7322-31-8
β-D-mannose

: 14168-65-1
mannosan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 1 h / 0 - 20 °C / Inert atmosphere 2: sodium hydroxide / 0 - 20 °C / Inert atmosphere View Scheme

: 108-24-7
acetic anhydride

: 14168-65-1
mannosan

: 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-Mannose pentaacetate

Conditions

Conditions	Yield
scandium tris(trifluoromethanesulfonate) at 20℃; for 5h;	95%

: 100-39-0
benzyl bromide

: 14168-65-1
mannosan

: 20888-02-2
1,6-anhydro-2,3,4-tri-O-benzyl-β-D-mannopyranose

Conditions

Conditions	Yield
Stage #1: mannosan With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 15 - 20℃; for 15h;	92%
With barium dihydroxide; barium(II) oxide In N,N-dimethyl-formamide for 1h; Ambient temperature; Yield given;
With tetra-(n-butyl)ammonium iodide; sodium hydride 1.) DMF, DMF; Multistep reaction;

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 14168-65-1
mannosan

: 388578-36-7
1,6-anhydro-2,3,4-tris-O-(triisopropylsilyl)-β-D-mannopyranose

Conditions

Conditions	Yield
With pyridine In 1,1,2,2-tetrachloroethane at 110℃; for 15h;	92%

: 29681-57-0
tert-butyldimethylsilane

: 14168-65-1
mannosan

A: 2,4-O-bis(t-butyldimethylsilyl)-1,6-anhydro-β-D-mannose

B: 2,3,4-tris(t-butyldimethylsilyl)-1,6-anhydro-β-D-mannose

Conditions

Conditions	Yield
With [Ir(COD)(PPh3)2]SbF6 In N,N-dimethyl acetamide at 70℃;	A 86% B 5%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 14168-65-1
mannosan

: 1,6-anhydro-2,3,4-tris-O-trimethylsilyl-β-D-mannopyranose

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	86%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 14168-65-1
mannosan

: 481704-39-6
1,6-anhydro-2,4-bis-O-(triisopropylsilyl)-β-D-mannopyranose

Conditions

Conditions	Yield
In pyridine; dichloromethane	80%

: 98-88-4
benzoyl chloride

: 14168-65-1
mannosan

: 1,6-anhydro-2-O-benzoyl-β-D-mannopyranoside

Conditions

Conditions	Yield
With iron(III)-acetylacetonate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 4h; Green chemistry; regioselective reaction;	78%

: 25023-01-2
9,9-dichloro-9H-fluorene

: 14168-65-1
mannosan

: 137016-99-0
1,6-anhydro-2,3-O-fluoren-9-ylidene-β-D-mannopyranose

Conditions

Conditions	Yield
With pyridine at 110℃; for 96h;	73%

: 100-39-0
benzyl bromide

: 14168-65-1
mannosan

: 116730-88-2
1,6-anhydro-2-O-benzyl-β-D-mannopyranoside

Conditions

Conditions	Yield
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 40℃; for 48h; Inert atmosphere; regioselective reaction;	73%

: 589-15-1
1-bromomethyl-4-bromobenzene

: 14168-65-1
mannosan

A: 1309382-38-4
1,6-anhydro-2-O-(4-bromobenzyl)-β-D-mannopyranoside

B: 1,6-anhydro-3-O-(4-bromobenzyl)-β-D-mannopyranoside

Conditions

Conditions	Yield
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 40℃; for 48h; Inert atmosphere; regioselective reaction;	A 73% B n/a

...Expand

: 939-26-4
2-bromomethylnaphthyl bromide

: 14168-65-1
mannosan

: 1309382-40-8
1,6-anhydro-2-O-(2-naphthyl)methyl-β-D-mannopyranoside

Conditions

Conditions	Yield
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 40℃; for 48h; Inert atmosphere; regioselective reaction;	71%

: 292638-85-8
acrylic acid methyl ester

: 14168-65-1
mannosan

: (1R,2R,3S,4S,5R)-2,4-dihydroxydihydro-5'H-6,8-dioxaspiro[bicyclo[3.2.1]octane-3,2'-furan]-5'-one

Conditions

Conditions	Yield
With Quinuclidine; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; oxybis(diphenylborane) In acetonitrile at 25℃; for 16h; Reagent/catalyst; Irradiation; Inert atmosphere; Schlenk technique; Sealed tube;	68%

: 1125-88-8
benzaldehyde dimethyl acetal

: 14168-65-1
mannosan

: 71049-45-1
1,6-anhydro-2,3-O-endo-benzylidene-β-D-mannopyranose

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 1h;	65.2%

: 100-39-0
benzyl bromide

: 14168-65-1
mannosan

A: 116429-52-8
1,6-anhydro-3-O-benzyl-β-D-mannopyranose

B: 116730-88-2
1,6-anhydro-2-O-benzyl-β-D-mannopyranoside

Conditions

Conditions	Yield
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.) 2 h;	A 25% B 65%
With 3 A molecular sieve; bis(tri-n-butyltin)oxide; 1-methyl-1H-imidazole; tetrabutylammomium bromide In toluene 1.) reflux, 15 h; 2.) 8 h;	A 38% B 52%

...Expand

: 108-32-7
1,2-propylene cyclic carbonate

: 14168-65-1
mannosan

poly(1,6-anhydro-β-D-mannopyranose-co-propylene carbonate): poly(1,6-anhydro-β-D-mannopyranose-co-propylene carbonate)

Conditions

Conditions	Yield
With 3-methyl-2-butynyltetramethylenesulfonium hexafluoroantimonate at 90℃; for 0.333333h;	64%

: 14168-65-1
mannosan

polymer, product of cationic polymerization, branching degree 0.44, Mw 1.050E4, PDI 1.43 by SEC, Mw 6.37E5 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose: polymer, product of cationic polymerization, branching degree 0.44, Mw 1.050E4, PDI 1.43 by SEC, Mw 6.37E5 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose

Conditions

Conditions	Yield
With 1-(2-butenyl)tetrahydrothiophenium hexafluoroantimonate In various solvent(s) at 150℃; for 0.666667h;	63%

: 3587-60-8
Benzyloxymethyl chloride

: 14168-65-1
mannosan

A: 1309382-41-9
1,6-anhydro-2-O-benzyloxymethyl-β-D-mannopyranoside

B: 1,6-anhydro-3-O-benzyloxymethyl-β-D-mannopyranoside

Conditions

Conditions	Yield
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 40℃; for 48h; Inert atmosphere; regioselective reaction;	A 63% B n/a

...Expand

: 14168-65-1
mannosan

polymer, product of cationic polymerization, branching degree 0.43, Mw 3.20E3, PDI 1.35 by SEC, Mw 8.05E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose: polymer, product of cationic polymerization, branching degree 0.43, Mw 3.20E3, PDI 1.35 by SEC, Mw 8.05E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose

Conditions

Conditions	Yield
With 1-(2-butenyl)tetrahydrothiophenium hexafluoroantimonate In various solvent(s) at 130℃; for 0.333333h;	61.6%

: 14168-65-1
mannosan

polymer, product of cationic polymerization, branching degree 0.43, Mw 4.30E3, PDI 1.49 by SEC, Mw 9.63E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose: polymer, product of cationic polymerization, branching degree 0.43, Mw 4.30E3, PDI 1.49 by SEC, Mw 9.63E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose

Conditions

Conditions	Yield
With 1-(2-butenyl)tetrahydrothiophenium hexafluoroantimonate In various solvent(s) at 150℃; for 0.333333h;	61.1%

: 14168-65-1
mannosan

polymer, product of cationic polymerization, branching degree 0.41, Mw 2.48E3, PDI 1.31 by SEC, Mw 6.94E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose: polymer, product of cationic polymerization, branching degree 0.41, Mw 2.48E3, PDI 1.31 by SEC, Mw 6.94E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose

Conditions

Conditions	Yield
With 1-(2-butenyl)tetrahydrothiophenium hexafluoroantimonate In various solvent(s) at 130℃; for 0.666667h;	57%

: 14168-65-1
mannosan

polymer, product of cationic polymerization, branching degree 0.42, Mw 2.17E3, PDI 1.30 by SEC, Mw 3.42E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose: polymer, product of cationic polymerization, branching degree 0.42, Mw 2.17E3, PDI 1.30 by SEC, Mw 3.42E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose

Conditions

Conditions	Yield
With 1-(2-butenyl)tetrahydrothiophenium hexafluoroantimonate In various solvent(s) at 130℃; for 0.333333h;	56.6%

: 77196-31-7
2-(dimethoxymethyl)naphthalene

: 14168-65-1
mannosan

A: 502690-08-6
endo-1,6-anhydro-2,3-O-(2-naphthyl)methylene-β-D-mannopyranose

B: exo-1,6-anhydro-2,3-O-(2-naphthyl)methylene-β-D-mannopyranose

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 24h;	A 55% B 9.2%

...Expand

: 54769-36-7
N-benzoyloxybenzotriazole

: 14168-65-1
mannosan

A: 1,6-anhydro-2-O-benzoyl-β-D-mannopyranoside

B: 676342-64-6
1,6-anhydro-2,4-di-O-benzoyl-β-D-mannopyranose

C: 5334-19-0
1,6-anhydro-2,3,4-tri-O-benzoyl-β-D-mannopyranose

Conditions

Conditions	Yield
With pyridine at 20℃; for 76h;	A 15% B 54% C 26%

...Expand

: 54769-36-7
N-benzoyloxybenzotriazole

: 14168-65-1
mannosan

: 676342-64-6
1,6-anhydro-2,4-di-O-benzoyl-β-D-mannopyranose

Conditions

Conditions	Yield
With pyridine	54%

: 1125-88-8
benzaldehyde dimethyl acetal

: 14168-65-1
mannosan

: 5349-10-0
1,6-anhydro-2,3-O-endo-benzylidene-β-mannopyranose

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; under 30 Torr; for 3h;	38%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 65 - 75℃; for 3h;	24%

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 14168-65-1
mannosan

A: 1,6-anhydro-endo-2,3-O-(4-methoxybenzylidene)-β-D-mannopyranose

B: 93793-97-6
1,6-Anhydro-endo-2,3-O-(4-methoxybenzylidene)-β-D-mannopyranose

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; under 225.023 Torr; for 4h; optical yield given as %de;	A n/a B 31%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide

...Expand

: 14168-65-1
mannosan

polymer, product of cationic polymerization, branching degree 0.44, Mw 5.84E3, PDI 1.84 by SEC, Mw 8.09E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose: polymer, product of cationic polymerization, branching degree 0.44, Mw 5.84E3, PDI 1.84 by SEC, Mw 8.09E4 by SLS; monomer(s): 1,6-anhydro-β-D-mannopyranose

Conditions

Conditions	Yield
With 1-(2-butenyl)tetrahydrothiophenium hexafluoroantimonate at 210℃; for 0.0166667h;	23.8%

1,6-Anhydro-beta-d-mannopyranose Specification

This chemical is called β-D-Mannopyranose, 1,6-anhydro-, and its systematic name is (1R,2S,3S,4S,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (non-preferred name). With the molecular formula of C₆H₁₀O₅, its molecular weight is 162.14. The CAS registry number of this chemical is 14168-65-1. Additionally, its product category is Carbohydrates & Derivatives.

Other characteristics of the β-D-Mannopyranose, 1,6-anhydro- can be summarised as followings: (1)ACD/LogP: -0.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.04; (4)ACD/LogD (pH 7.4): -0.04; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 22.6; (8)ACD/KOC (pH 7.4): 22.6; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 46.15 Å²; (13)Index of Refraction: 1.619; (14)Molar Refractivity: 33.7 cm³; (15)Molar Volume: 95.9 cm³; (16)Polarizability: 13.36×10^-24cm³; (17)Surface Tension: 70.6 dyne/cm; (18)Density: 1.688 g/cm³; (19)Flash Point: 185.9 °C; (20)Enthalpy of Vaporization: 73.13 kJ/mol; (21)Boiling Point: 383.8 °C at 760 mmHg; (22)Vapour Pressure: 1.81E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: O[C@H]2[C@@H](O)[C@H](O)[C@@H]1O[C@H]2OC1
2.InChI: InChI=1/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5+,6-/m1/s1
3.InChIKey: TWNIBLMWSKIRAT-RWOPYEJCBN

Product Name

1,6-Anhydro-beta-d-mannopyranose

Synthetic route

1,6-Anhydro-beta-d-mannopyranose Specification

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