5934-56-5

Basic information

• Product Name: L-(-)-IDOSE
• Synonyms: L-(-)-IDOSE;L-IDOSE;L-(-)-idose minimum 95%;L-(-)-Idose 0.1M aqueous solution;(3R,4S,5S,6S)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrol;L-Idose - Aqueous solution;L-idose (0.145M solution)
• CAS NO: 5934-56-5
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.16
• EINECS: 227-688-7
• Mol File: 5934-56-5.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 527.1°C at 760 mmHg
• Flash Point: 286.7°C
• Appearance: /
• Density: 1.581g/cm³
• Vapor Pressure: 2.59E-13mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: Refrigerator
• Solubility: Methanol (Slightly), Water (Soluble)
• PKA: 12.45±0.20(Predicted)
• CAS DataBase Reference: L-(-)-IDOSE(CAS DataBase Reference)
• NIST Chemistry Reference: L-(-)-IDOSE(5934-56-5)
• EPA Substance Registry System: L-(-)-IDOSE(5934-56-5)

Safety Data

• Hazardous Substances Data: 5934-56-5(Hazardous Substances Data)

Usage

Uses

L-Isomer of D-Idose (I175050), a monosaccharide that has is an important component of dermatan sulfate and heparan sulfate.

InChI:InChI=1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4-,5+,6+/m0/s1

Synthetic route

1,2-O-isopropylidene-β-L-idofuranose (29747-91-9) → glucose (5934-56-5) + 1,6-anhydro-β-D-idopyranose (60619-47-8)

Conditions	Yield
sulfuric acid In water at 50℃; for 3.5h;	A 92% B 1%

5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose (4118-60-9) → glucose (5934-56-5) + 1,6-anhydro-β-D-idopyranose (60619-47-8)

Conditions	Yield
With sulfuric acid In water at 100℃; for 6h;	A 10% B 88%

5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose (4118-60-9) → glucose (5934-56-5) + 2,5-anhydro-D-glucose (18439-33-3)

Conditions	Yield
With sulfuric acid In water at 50 - 60℃; for 3.5h;	A 85% B 12%

((2S,3R,4S,5R)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-methanol (221015-77-6) → glucose (5934-56-5)

Conditions	Yield
With hydrogen; palladium dihydroxide In methanol for 144h; Ambient temperature;	80%

5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose (4118-60-9) → glucose (5934-56-5) + 2,5-anhydro-D-glucose (18439-33-3) + 1,2-O-isopropylidene-β-L-idofuranose (29747-91-9)

Conditions	Yield
sulfuric acid In water at 50℃; for 8h;	A 76% B 14% C 5%
sulfuric acid In water at 45℃; for 2.5h;	A 15% B 7% C 62%

(2R,3S,4R,5S)-6-Benzhydryloxy-2,3,4,5-tetrahydroxy-hexanal → glucose (5934-56-5)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol Yield given;

6,7-dideoxy-L-ido-hept-6-enitol (143168-78-9) → glucose (5934-56-5)

Conditions	Yield
With ozone; sodium sulfite 1.) MeOH, -78 deg C, 2. a) -78 deg C, 1 h, b) r.t., 15 h; Yield given. Multistep reaction;

O1,O2-isopropylidene β-L-idofuranose → glucose (5934-56-5)

Conditions	Yield
With sulfuric acid

L-idonic acid (1114-17-6) + sodium amalgam + acid → glucose (5934-56-5)

Conditions	Yield
das Lacton reagiert;

(2R,3S,4R)-2,3,4-Tris-benzyloxymethoxy-4-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-yl]-butyraldehyde → glucose (5934-56-5)

Conditions	Yield
With hydrogen; palladium dihydroxide In tetrahydrofuran; water

L-gulose (6027-89-0) → L-sorbose (87-79-6) + L-tagatose (17598-82-2) + glucose (5934-56-5)

Conditions	Yield
Stage #1: L-gulose With aluminum oxide In pyridine for 2h; Heating; Stage #2: With sulfuric acid In acetone for 2h; Further stages.;	A 70 % Chromat. B 7 % Chromat. C 10 % Chromat.

L-sorbose (87-79-6) → L-tagatose (17598-82-2) + L-gulose (6027-89-0) + glucose (5934-56-5)

Conditions	Yield
Stage #1: L-sorbose With aluminum oxide In pyridine for 4h; Heating; Stage #2: With sulfuric acid In acetone for 2h; Further stages.;	A 6 % Chromat. B 8 % Chromat. C 6 % Chromat.

(E)-3-(2-furanyl)-2-propen-1-ol (27393-97-1, 79380-02-2) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 18 steps 1: 98 percent / DMAP / CH2Cl2 / 4 h / Ambient temperature 2: 94 percent / MeSO2NH2, AD-mix-β / 2-methyl-propan-2-ol; H2O / 95 h / 0 °C 3: MCPBA, NaHCO3 / CH2Cl2 / 3 h / Ambient temperature 4: p-TSOH / benzene / 5 h / Heating 5: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.42 h / 0 °C 6: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h 7: 94 percent / NMO, OsO4, H2O / acetone; tetrahydrofuran / 3 h / Ambient temperature 8: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h 9: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 10: Et3N / CH2Cl2 / 3 h / Ambient temperature 11: LiI / tetrahydrofuran / 6 h / Heating 12: 97 percent / Zn, AcOH / 3 h / Ambient temperature 13: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 14: 74 percent / DABCO / benzene / 15 h / Ambient temperature 15: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 16: 88 percent / p-TsOH / benzene / 7 h / Heating 17: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 18: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

tert-Butyl-((E)-3-furan-2-yl-allyloxy)-dimethyl-silane (221015-42-5) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 17 steps 1: 94 percent / MeSO2NH2, AD-mix-β / 2-methyl-propan-2-ol; H2O / 95 h / 0 °C 2: MCPBA, NaHCO3 / CH2Cl2 / 3 h / Ambient temperature 3: p-TSOH / benzene / 5 h / Heating 4: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.42 h / 0 °C 5: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h 6: 94 percent / NMO, OsO4, H2O / acetone; tetrahydrofuran / 3 h / Ambient temperature 7: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h 8: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 9: Et3N / CH2Cl2 / 3 h / Ambient temperature 10: LiI / tetrahydrofuran / 6 h / Heating 11: 97 percent / Zn, AcOH / 3 h / Ambient temperature 12: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 13: 74 percent / DABCO / benzene / 15 h / Ambient temperature 14: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 15: 88 percent / p-TsOH / benzene / 7 h / Heating 16: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 17: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one (221015-46-9) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 14 steps 1: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.42 h / 0 °C 2: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h 3: 94 percent / NMO, OsO4, H2O / acetone; tetrahydrofuran / 3 h / Ambient temperature 4: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h 5: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 6: Et3N / CH2Cl2 / 3 h / Ambient temperature 7: LiI / tetrahydrofuran / 6 h / Heating 8: 97 percent / Zn, AcOH / 3 h / Ambient temperature 9: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 10: 74 percent / DABCO / benzene / 15 h / Ambient temperature 11: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 12: 88 percent / p-TsOH / benzene / 7 h / Heating 13: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 14: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(1R,2S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-ol (221015-49-2) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 13 steps 1: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h 2: 94 percent / NMO, OsO4, H2O / acetone; tetrahydrofuran / 3 h / Ambient temperature 3: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h 4: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 5: Et3N / CH2Cl2 / 3 h / Ambient temperature 6: LiI / tetrahydrofuran / 6 h / Heating 7: 97 percent / Zn, AcOH / 3 h / Ambient temperature 8: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 9: 74 percent / DABCO / benzene / 15 h / Ambient temperature 10: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 11: 88 percent / p-TsOH / benzene / 7 h / Heating 12: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 13: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(1S,2R)-3-(tert-Butyl-dimethyl-silanyloxy)-1-furan-2-yl-propane-1,2-diol (221015-44-7) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 16 steps 1: MCPBA, NaHCO3 / CH2Cl2 / 3 h / Ambient temperature 2: p-TSOH / benzene / 5 h / Heating 3: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.42 h / 0 °C 4: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h 5: 94 percent / NMO, OsO4, H2O / acetone; tetrahydrofuran / 3 h / Ambient temperature 6: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h 7: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 8: Et3N / CH2Cl2 / 3 h / Ambient temperature 9: LiI / tetrahydrofuran / 6 h / Heating 10: 97 percent / Zn, AcOH / 3 h / Ambient temperature 11: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 12: 74 percent / DABCO / benzene / 15 h / Ambient temperature 13: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 14: 88 percent / p-TsOH / benzene / 7 h / Heating 15: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 16: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-6-hydroxy-6H-pyran-3-one → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 15 steps 1: p-TSOH / benzene / 5 h / Heating 2: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.42 h / 0 °C 3: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h 4: 94 percent / NMO, OsO4, H2O / acetone; tetrahydrofuran / 3 h / Ambient temperature 5: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h 6: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 7: Et3N / CH2Cl2 / 3 h / Ambient temperature 8: LiI / tetrahydrofuran / 6 h / Heating 9: 97 percent / Zn, AcOH / 3 h / Ambient temperature 10: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 11: 74 percent / DABCO / benzene / 15 h / Ambient temperature 12: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 13: 88 percent / p-TsOH / benzene / 7 h / Heating 14: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 15: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

((1R,2S,5S,7R)-2-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-en-7-ylmethoxy)-tert-butyl-dimethyl-silane (221015-50-5) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 12 steps 1: 94 percent / NMO, OsO4, H2O / acetone; tetrahydrofuran / 3 h / Ambient temperature 2: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h 3: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 4: Et3N / CH2Cl2 / 3 h / Ambient temperature 5: LiI / tetrahydrofuran / 6 h / Heating 6: 97 percent / Zn, AcOH / 3 h / Ambient temperature 7: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 8: 74 percent / DABCO / benzene / 15 h / Ambient temperature 9: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 10: 88 percent / p-TsOH / benzene / 7 h / Heating 11: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 12: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(1S,2S,3R,4S,5S,7R)-2-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]octane-3,4-diol (221015-52-7) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 11 steps 1: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h 2: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 3: Et3N / CH2Cl2 / 3 h / Ambient temperature 4: LiI / tetrahydrofuran / 6 h / Heating 5: 97 percent / Zn, AcOH / 3 h / Ambient temperature 6: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 7: 74 percent / DABCO / benzene / 15 h / Ambient temperature 8: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 9: 88 percent / p-TsOH / benzene / 7 h / Heating 10: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 11: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ol → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 6 steps 1: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 2: 74 percent / DABCO / benzene / 15 h / Ambient temperature 3: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 4: 88 percent / p-TsOH / benzene / 7 h / Heating 5: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 6: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ol → glucose (5934-56-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / p-TsOH / benzene / 7 h / Heating 2: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 3: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-one (221015-69-6) → glucose (5934-56-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 74 percent / DABCO / benzene / 15 h / Ambient temperature 2: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 3: 88 percent / p-TsOH / benzene / 7 h / Heating 4: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 5: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-one (221015-71-0) → glucose (5934-56-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 2: 88 percent / p-TsOH / benzene / 7 h / Heating 3: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 4: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

((1S,2S,3S,4S,5S,7R)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol (221015-56-1) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 9 steps 1: Et3N / CH2Cl2 / 3 h / Ambient temperature 2: LiI / tetrahydrofuran / 6 h / Heating 3: 97 percent / Zn, AcOH / 3 h / Ambient temperature 4: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 5: 74 percent / DABCO / benzene / 15 h / Ambient temperature 6: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 7: 88 percent / p-TsOH / benzene / 7 h / Heating 8: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 9: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

(1R,2S,3S,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane (221015-58-3) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 7 steps 1: 97 percent / Zn, AcOH / 3 h / Ambient temperature 2: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 3: 74 percent / DABCO / benzene / 15 h / Ambient temperature 4: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 5: 88 percent / p-TsOH / benzene / 7 h / Heating 6: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 7: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

Methanesulfonic acid (1S,2S,3S,4S,5S,7R)-2,3,4-tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethyl ester → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 8 steps 1: LiI / tetrahydrofuran / 6 h / Heating 2: 97 percent / Zn, AcOH / 3 h / Ambient temperature 3: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 4: 74 percent / DABCO / benzene / 15 h / Ambient temperature 5: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 6: 88 percent / p-TsOH / benzene / 7 h / Heating 7: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 8: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

ethyl (E)-3-(2-furyl)prop-2-enoate (623-20-1) → glucose (5934-56-5)

Conditions

Yield

Multi-step reaction with 19 steps 1: 97 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 2: 98 percent / DMAP / CH2Cl2 / 4 h / Ambient temperature 3: 94 percent / MeSO2NH2, AD-mix-β / 2-methyl-propan-2-ol; H2O / 95 h / 0 °C 4: MCPBA, NaHCO3 / CH2Cl2 / 3 h / Ambient temperature 5: p-TSOH / benzene / 5 h / Heating 6: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.42 h / 0 °C 7: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h 8: 94 percent / NMO, OsO4, H2O / acetone; tetrahydrofuran / 3 h / Ambient temperature 9: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h 10: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature 11: Et3N / CH2Cl2 / 3 h / Ambient temperature 12: LiI / tetrahydrofuran / 6 h / Heating 13: 97 percent / Zn, AcOH / 3 h / Ambient temperature 14: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH2Cl2 / 1.5 h / Ambient temperature 15: 74 percent / DABCO / benzene / 15 h / Ambient temperature 16: 96 percent / DIBAL / CH2Cl2; toluene / 2 h / -78 °C 17: 88 percent / p-TsOH / benzene / 7 h / Heating 18: 1.) O3, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 10 min, 2.) MeOH, CH2Cl2, -78 deg C to r.t. 19: 80 percent / H2 / Pd(OH)2 / methanol / 144 h / Ambient temperature View Scheme

5,6-dideoxy-L-xylo-hept-5-en-2-ulose (143106-71-2) → glucose (5934-56-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / phosphate buffer (pH 7.0), sodium formate, NADH sodium salt / H2O / 72 h / Ambient temperature; sorbitol dehydrogenase (EC 1.1.1.14) from sheep liver, formate dehydrogenase (EC 1.2.1.2) from yeast 2: 1.) O3, 2.) Na2SO3 / 1.) MeOH, -78 deg C, 2. a) -78 deg C, 1 h, b) r.t., 15 h View Scheme

glucose (5934-56-5) + phenylhydrazine acetate (72358-76-0) → lyxo-[2]Hexosulose-bis-phenylhydrazon (23275-67-4)

Conditions	Yield
phenyl-l-sorbosazone;

glucose (5934-56-5) → L-iditol (488-45-9)

Conditions	Yield
With water; nickel at 95℃; Hydrogenation.unter Druck;
With monospecific xylose reductase from yeast Candida intermedia; NADPH In phosphate buffer at 25℃; pH=7.0; Enzyme kinetics; Further Variations:; Reagents;

glucose (5934-56-5) → D-iditol (25878-23-3)

Conditions	Yield
With sodium amalgam

glucose (5934-56-5) → L-sorbose (87-79-6)

Conditions	Yield
beim Aufbewahren;

glucose (5934-56-5) → L-idaric acid ; dipotassium L idarate (576-42-1, 18404-47-2, 18404-62-1, 36439-43-7, 84864-60-8, 84878-11-5)

Conditions	Yield
With nitric acid; potassium carbonate 1.) heating.; Yield given. Multistep reaction;

Upstream product

• 29747-91-9 1,2-O-isopropylidene-β-L-idofuranose 
• 481-74-3 Chrysophanol 
• 56-82-6 Glyceraldehyde 
• 926646-14-2 D-glucose-imine 
• 118923-30-1 D-glucitol-1-yliden-urea 
• 7647-01-0 hydrogenchloride 
• 1941-52-2 D-glucose diethyl mercaptal 
• 4990-72-1 glucosealdazine 
• 18604-50-7 eugenyl glucoside 
• 7664-93-9 sulfuric acid 
• 50-00-0 formaldehyd 
• 962-53-8 DL-galactose-phenylhydrazone 
• 608-66-2 D-galactitol 
• 133-42-6 galactonic acid 

Downstream Products

• 4875-10-9 o-nitrothiophenol 
• 110-15-6 succinic acid 
• 849585-22-4 LACTIC ACID 
• 67-64-1 acetone 
• 23275-67-4 lyxo-[2]Hexosulose-bis-phenylhydrazon 
• 488-45-9 L-iditol 
• 25878-23-3 D-iditol 
• 87-79-6 L-sorbose 
• 64-18-6 formic acid 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 79-14-1 glycolic Acid 
• 69-65-8 mannitol 
• 60660-58-4 L-altritol 
• 488-69-7 fructose-1,6-bisphosphate 

Relevant articles and documents

13C-Labeled Idohexopyranosyl Rings: Effects of Methyl Glycosidation and C6 Oxidation on Ring Conformational Equilibria

An ensemble of JHH, JCH, and JCC values was measured in aqueous solutions of methyl α- and β-d-idohexopyranosides containing selective 13C-enrichment at various carbons. By comparing these J-couplings to those reported previously in the α- and β-d-idohexopyranoses, methyl glycosidation was found to affect ring conformational equilibria, with the percentages of 4C1 forms based on 3JHH analysis as follows: α-d-idopyranose, methyl α-d-idopyranoside, methyl β-d-idopyranoside, β-d-idopyranose, 82%. JCH and JCC values were analyzed with assistance from theoretical values obtained from density functional theory (DFT) calculations. Linearized plots of the percentages of 4C1 against limiting JCH and JCC values in the chair forms were used to (a) determine the compatibility of the experimental JCH and JCC values with 4C1/1C4 ratios determined from JHH analysis and (b) determine the sensitivity of specific JCH and JCC values to ring conformation. Ring conformational equilibria for methyl idohexopyranosides differ significantly from those predicted from recent molecular dynamics (MD) simulations, indicating that equilibria determined by MD for ring configurations with energetically flat pseudorotational itineraries may not be quantitative. J-couplings in methyl α-l-[6-13C]idopyranosiduronic acid and methyl α-d-[6-13C]glucopyranosiduronic acid were measured as a function of solution pH. The ring conformational equilibrium is pH-dependent in the iduronic acid.

Orthogonal Active-Site Labels for Mixed-Linkage endo-β-Glucanases

Small molecule irreversible inhibitors are valuable tools for determining catalytically important active-site residues and revealing key details of the specificity, structure, and function of glycoside hydrolases (GHs). β-glucans that contain backbone β(1,3) linkages are widespread in nature, e.g., mixed-linkage β(1,3)/β(1,4)-glucans in the cell walls of higher plants and β(1,3)glucans in yeasts and algae. Commensurate with this ubiquity, a large diversity of mixed-linkage endoglucanases (MLGases, EC 3.2.1.73) and endo-β(1,3)-glucanases (laminarinases, EC 3.2.1.39 and EC 3.2.1.6) have evolved to specifically hydrolyze these polysaccharides, respectively, in environmental niches including the human gut. To facilitate biochemical and structural analysis of these GHs, with a focus on MLGases, we present here the facile chemo-enzymatic synthesis of a library of active-site-directed enzyme inhibitors based on mixed-linkage oligosaccharide scaffolds and N-bromoacetylglycosylamine or 2-fluoro-2-deoxyglycoside warheads. The effectiveness and irreversibility of these inhibitors were tested with exemplar MLGases and an endo-β(1,3)-glucanase. Notably, determination of inhibitor-bound crystal structures of a human-gut microbial MLGase from Glycoside Hydrolase Family 16 revealed.

Method for preparing lactic acid through catalytically converting carbohydrate

The invention relates to a method for preparing lactic acid through catalytically converting carbohydrate, and in particular, relates to a process for preparing lactic acid by catalytically convertingcarbohydrate under hydrothermal conditions. The method disclosed by the invention is characterized by specifically comprising the following steps: 1) adding carbohydrate and a catalyst into a closedhigh-pressure reaction kettle, and then adding pure water for mixing; 2) introducing nitrogen into the high-pressure reaction kettle to discharge air, introducing nitrogen of 2 MPa, stirring and heating to 160-300 DEG C, and carrying out reaction for 10-120 minutes; 3) putting the high-pressure reaction kettle in an ice-water bath, and cooling to room temperature; and 4) filtering the solution through a microporous filtering membrane to obtain the target product. The method can realize high conversion rate of carbohydrate and high yield of lactic acid, and has the advantages of less catalyst consumption, good circularity, small corrosion to reaction equipment and the like.