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[ CAS No. 22415-91-4 ] {[proInfo.proName]}

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Chemical Structure| 22415-91-4
Chemical Structure| 22415-91-4
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Product Details of [ 22415-91-4 ]

CAS No. :22415-91-4 MDL No. :MFCD00010695
Formula : C41H32O11 Boiling Point : -
Linear Structure Formula :- InChI Key :JJNMLNFZFGSWQR-MJSUJZIKSA-N
M.W : 700.69 Pubchem ID :10930521
Synonyms :

Safety of [ 22415-91-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22415-91-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 22415-91-4 ]

[ 22415-91-4 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 492-62-6 ]
  • [ 98-88-4 ]
  • [ 22415-91-4 ]
YieldReaction ConditionsOperation in experiment
96% With pyridine; dmap; at 20℃; for 6h; D-glucose (900 mg, 5 mmo 1),DMAP (244 mg, 2 mmol) was dissolved in anhydrous pyridine (30 mL)Benzoyl chloride (5 mL) was added,Room temperature reaction for 6 hours.After the reaction is complete,To the reaction solution was added dilute hydrochloric acid (100 ml)Ethyl acetate (30 ml X)Combine organic phase,Saturated brine (30 ml X 2)Anhydrous Na2S04 dry, concentrated,(PE: EpsilonAlpha = 3: 1)To give a white solid (3.36 g, 96%) as shown in formula (A-1).
89% With pyridine; at 0 - 20℃; for 2.16667h; 2,3,4,6-Tetra-O-benzoyl-a-D-glucopyranosyl Benzoate (2) Benzoyl chloride (4.68 g, 33.3 mmol) was added dropwise to a solution of a-D-glucose (1.0 g, 5.6 mmol) in pyridine (30 mL) at 0C. After 10 min at 0C, the solution was stirred for 2 hrs at room temperature. The reaction was quenched by addition of cold water (50 mL) and the product extracted with EtOAc (3 x 50 ml). The combined organic layers were washed with 1 N HCI (3 x 50 mL) followed by brine (50 mL) and then dried, filtered and concentrated. The crude product was purified by recrystallisation with hot Hexane: EtOAc 2:1 to give the title compound as a white solid (3.48 g, 89%). Rf = 0.28 (Hex: EtOAc 8:2). deltaEta (CDCI3, 400 MHz): 8.16 (2H, d, J = 8.0 Hz, H-Ar), 8.02 (2H, d, J = 8.0 Hz, H-Ar), 7.94 (2H, d, J = 8.0 Hz, H-Ar), 7.88 (4H, d, J = 8.0 Hz, H-Ar), 7.66 (1 H, t, J = 8.0 Hz, H-Ar), 7.53-7.28 (14H, m, H-Ar), 6.85 (1 H, d, J = 4.0 Hz, H-1 ), 6.32 (1 H, t, J = 8.0 Hz, H-3), 5.85 (1 H, t, J = 8.0 Hz, H-4), 5.68 (1 H, dd, J = 4.0, 8.0 Hz, H-2), 4.62 (2H, m, H-6a/H-5), 4.59 (1 H, dd, J = 4.0 Hz, J = 12.0 Hz, H-6b) 5C (CDCI3, 100 MHz): 166.1 , 165.9, 165.3, 165.1 , 164.4 (C=0), [133.9, 133.5, 133.4, 133.3, 133.1 130.0, 129.9 (x2), 129.8 (x2), 129.6, 129.0, 128.9, 128.8, 128.6, 128.4 (x3), 128.37 ArC)], 90.0 (C-1 ), 76.6 (C-3), 70.5 (C-2), 70.5 (C-5), 68.9 (C-4), 62.5 (C-6)
63% With pyridine; dmap; at 0 - 20℃; for 16h;Inert atmosphere; BzCl (3.9 mL, 33.3 mmol) was added dropwise with stirring to D-glucose (1.0 g, 5.6 mmol) and DMAP(136 mg, 1.11 mmol) in pyridine (28 mL) at 0 C and the mixture was allowed to warm to roomtemperature. After 16 h, cold H2O (50 mL) was added and the mixture extracted with EtOAc (2 × 100mL). The combined organic layers were washed with aqueous HCl (1.0 M; 2 × 100 mL), brine (50 mL),and dried (MgSO4) and rotary evaporated to give the crude product. Recrystallization from EtOAc andhexanes gave the pentabenzoate 40 (2.46 g, 63%) as a white solid
  • 2
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 22415-91-4 ]
YieldReaction ConditionsOperation in experiment
With benzoic acid; zinc(II) chloride
  • 3
  • [ 22415-91-4 ]
  • [ 14218-11-2 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen bromide; acetic acid In dichloromethane at 0 - 20℃;
93% With hydrogen bromide; acetic acid In dichloromethane at 20℃; for 3h; Inert atmosphere; Cooling with ice; 2 2. Preparation method of compound 2-1: Under nitrogen protection, The perbenzoyl protected glucose (58 g) was dissolved in dry DCM (100 mL). Stir at room temperature and add HBr/HOAc (61 mL) under ice bath. Slowly warm to room temperature, stir at room temperature for 3 h, dilute with DCM, wash three times with water. Saturated with sodium bicarbonate three times, Wash once with saturated sodium chloride and dry the organic phase with anhydrous sodium sulfate. The compound was suspended by filtration to give a white solid 51 g (yield: 93%).
83% With trimethylsilyl bromide; cholesterol; zinc dibromide In dichloromethane at 5℃; for 3h;
83% With hydrogen bromide In dichloromethane; acetic acid at 0℃;
With hydrogen bromide; acetic acid
With hydrogen bromide; acetic acid; 1,2-dichloro-ethane
With hydrogen bromide; acetic anhydride; acetic acid In dichloromethane at 0℃;

  • 5
  • [ 22415-91-4 ]
  • [ 762-72-1 ]
  • [ 98920-47-9 ]
  • [ 98854-01-4 ]
YieldReaction ConditionsOperation in experiment
1: 2.3% 2: 60% With boron trifluoride diethyl etherate In acetonitrile at 80℃;
  • 6
  • [ 22415-91-4 ]
  • [ 34820-17-2 ]
  • [ 627466-64-2 ]
YieldReaction ConditionsOperation in experiment
1: 60% 2: 10% With bis(tri-n-butyltin)oxide In toluene for 24h; Heating;
  • 7
  • [ 22415-91-4 ]
  • [ 15356-13-5 ]
  • [ 1863-63-4 ]
  • [ 116143-85-2 ]
  • [ 116143-92-1 ]
  • 8
  • [ 22415-91-4 ]
  • [ 15356-13-5 ]
  • [ 66530-18-5 ]
  • [ 116143-85-2 ]
  • [ 116143-92-1 ]
YieldReaction ConditionsOperation in experiment
1: 29% 2: 11.9% 3: 9.6% 4: 2.4% With ammonia In 1,4-dioxane; chloroform at -60℃; for 100h;
  • 9
  • [ 22415-91-4 ]
  • [ 15356-13-5 ]
  • [ 116143-85-2 ]
  • [ 116143-94-3 ]
  • [ 116143-92-1 ]
YieldReaction ConditionsOperation in experiment
1: 29% 2: 11.9% 3: 9.6% 4: 2.1% With ammonia In 1,4-dioxane; chloroform at -60℃; for 100h; Further byproducts given;
  • 10
  • [ 22415-91-4 ]
  • [ 15356-13-5 ]
  • [ 116143-85-2 ]
  • [ 116143-98-7 ]
  • [ 116143-92-1 ]
YieldReaction ConditionsOperation in experiment
1: 11.9% 2: 9.6% 3: 5.4% 4: 29% With ammonia In 1,4-dioxane; chloroform at -60℃; for 100h; Further byproducts given;
  • 11
  • [ 22415-91-4 ]
  • [ 15356-13-5 ]
  • [ 55-21-0 ]
  • [ 116143-85-2 ]
  • [ 116143-92-1 ]
YieldReaction ConditionsOperation in experiment
1: 29% 2: 11.9% 3: 9.6% 4: 18.1 mg With ammonia In 1,4-dioxane; chloroform at -60℃; for 100h; Further byproducts given;
  • 12
  • [ 22415-91-4 ]
  • [ 627466-64-2 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With hydrogen bromide; acetic acid In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; Stage #2: With silver (II) carbonate In water; acetone at 20℃; for 2h;
90% With sodium methylate In tetrahydrofuran for 0.216667h;
83% With methylamine In tetrahydrofuran; methanol at 20℃; for 2h;
60% With ammonium carbonate In tetrahydrofuran; methanol at 30℃; for 30h;
With hydrazinium monoacetate In N,N-dimethyl-formamide at 20℃; for 30h;

  • 13
  • [ 22415-91-4 ]
  • [ 75860-53-6 ]
YieldReaction ConditionsOperation in experiment
22% With bromine In tetrachloromethane for 4h; Heating; Irradiation;
  • 14
  • [ 22415-91-4 ]
  • [ 116143-85-2 ]
  • [ 116144-02-6 ]
  • [ 116143-98-7 ]
  • [ 116143-92-1 ]
YieldReaction ConditionsOperation in experiment
1: 11.9% 2: 9.6% 3: 5.4% 4: 0.7% With ammonia In 1,4-dioxane; chloroform at -60℃; for 100h; Further byproducts given;
  • 15
  • [ 22415-91-4 ]
  • [ 116143-85-2 ]
  • [ 116143-89-6 ]
  • [ 116143-98-7 ]
  • [ 116143-92-1 ]
YieldReaction ConditionsOperation in experiment
1: 11.9% 2: 9.6% 3: 5.4% 4: 1.4% With ammonia In 1,4-dioxane; chloroform at -60℃; for 100h; Further byproducts given;
  • 16
  • [ 22415-91-4 ]
  • [ 116143-85-2 ]
  • [ 116143-98-7 ]
  • [ 116143-95-4 ]
  • [ 116143-92-1 ]
YieldReaction ConditionsOperation in experiment
1: 11.9% 2: 9.6% 3: 5.4% 4: 0.2% With ammonia In 1,4-dioxane; chloroform at -60℃; for 100h; Further byproducts given;
  • 17
  • [ 492-61-5 ]
  • [ 93-97-0 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 22415-91-4 ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-3-methyl-imidazolium benzoate In various solvent(s) at 20℃; for 5.5h; Title compound not separated from byproducts;
  • 18
  • [ 492-62-6 ]
  • [ 93-97-0 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 22415-91-4 ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-3-methyl-imidazolium benzoate at 20℃; for 5h; Title compound not separated from byproducts;
  • 19
  • [ 50-99-7 ]
  • [ 98-88-4 ]
  • [ 22415-91-4 ]
YieldReaction ConditionsOperation in experiment
95% In pyridine at 0℃; for 2h;
  • 21
  • [ 50-99-7 ]
  • [ 98-88-4 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 22415-91-4 ]
YieldReaction ConditionsOperation in experiment
1: 2.0 mg 2: 0.8 mg With pyridine at 20℃; for 12h;
  • 22
  • [ 22415-91-4 ]
  • [ 151767-11-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / methylamine / methanol; tetrahydrofuran / 2 h / 20 °C 2: 91 percent / Cs2CO3 / CH2Cl2 / 2 h / 20 °C
  • 23
  • [ 22415-91-4 ]
  • [ 617698-87-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 83 percent / methylamine / methanol; tetrahydrofuran / 2 h / 20 °C 2.1: 91 percent / Cs2CO3 / CH2Cl2 / 2 h / 20 °C 3.1: 4 Angstroem molecular sieves / CH2Cl2 / 0.25 h / 20 °C 3.2: 83 percent / Sn(OTf)2 / CH2Cl2 / 2 h
  • 24
  • [ 22415-91-4 ]
  • 4-(hydroxymethyl)benzyl 3-O-(4-azido-3-chlorobenzyl)-4,6-di-O-benzyl-β-D-glucopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->6)]-4,6-di-O-benzyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-benzyl-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 83 percent / methylamine / methanol; tetrahydrofuran / 2 h / 20 °C 2.1: 91 percent / Cs2CO3 / CH2Cl2 / 2 h / 20 °C 3.1: 4 Angstroem molecular sieves / CH2Cl2 / 0.25 h / 20 °C 3.2: 83 percent / Sn(OTf)2 / CH2Cl2 / 2 h
  • 25
  • [ 22415-91-4 ]
  • [ 148926-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: H2O; NBS / acetonitrile / 20 °C
Multi-step reaction with 6 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C 6: 92 percent / H2O; NBS / acetonitrile / 20 °C
Multi-step reaction with 6 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: 97 percent / 4-pentenol; TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C 6: 92 percent / H2O; NBS / acetonitrile / 20 °C
  • 26
  • [ 22415-91-4 ]
  • [ 479623-62-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: H2O; NBS / acetonitrile / 20 °C
Multi-step reaction with 5 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C
  • 27
  • [ 22415-91-4 ]
  • Benzoic acid (2S,3R,4S,5R,6R)-2-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: H2O; NBS / acetonitrile / 20 °C 6: DMAP; pyridine / CH2Cl2 / 20 °C
Multi-step reaction with 7 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C 6: 92 percent / H2O; NBS / acetonitrile / 20 °C 7: DMAP; pyridine / CH2Cl2 / 20 °C
Multi-step reaction with 7 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: 97 percent / 4-pentenol; TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C 6: 92 percent / H2O; NBS / acetonitrile / 20 °C 7: DMAP; pyridine / CH2Cl2 / 20 °C
  • 28
  • [ 22415-91-4 ]
  • [ 297747-11-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating
  • 29
  • [ 22415-91-4 ]
  • [ 417705-97-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C
Multi-step reaction with 5 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: 97 percent / 4-pentenol; TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C
  • 30
  • [ 22415-91-4 ]
  • [ 479623-59-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran
  • 31
  • [ 22415-91-4 ]
  • 3,4,6-tri-O-benzyl-α-D-glucopyranose 1,2-(isopropyl orthobenzoate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: 78 percent / iodonium dicollidine triflate / CH2Cl2 / 0.5 h / 20 °C
  • 32
  • [ 22415-91-4 ]
  • Benzoic acid (2R,3R,4S,5R,6R)-2-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: H2O; NBS / acetonitrile / 20 °C 6: DMAP; pyridine / CH2Cl2 / 20 °C
Multi-step reaction with 7 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C 6: 92 percent / H2O; NBS / acetonitrile / 20 °C 7: DMAP; pyridine / CH2Cl2 / 20 °C
Multi-step reaction with 7 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: 97 percent / 4-pentenol; TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C 6: 92 percent / H2O; NBS / acetonitrile / 20 °C 7: DMAP; pyridine / CH2Cl2 / 20 °C
  • 33
  • [ 22415-91-4 ]
  • Benzoic acid (2R,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: H2O; NBS / acetonitrile / 20 °C 6: DMAP; pyridine / CH2Cl2
Multi-step reaction with 6 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: TBDMSOTf / CH2Cl2 / 0.03 h / 20 °C 6: DMAP; pyridine / CH2Cl2
  • 34
  • [ 22415-91-4 ]
  • [ 479623-60-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C
  • 35
  • [ 22415-91-4 ]
  • 3,4,6-tri-O-benzyl-O-α-D-glucopyranose 1,2-(benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl orthobenzoate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: 65 percent / iodonium dicollidine triflate; molecular sieves / CH2Cl2; toluene / 0.5 h / 20 °C
  • 36
  • [ 22415-91-4 ]
  • [ 479623-70-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Ac2O; 30 percent HBr/AcOH / CH2Cl2 / 0 °C 2: 2,6-lutidine; Bu4NI / CH2Cl2 / Heating 3: NaOMe / methanol; tetrahydrofuran 4: 84 percent / imidazole; NaH / dimethylformamide / 2 h / 70 °C 5: 73 percent / NBS; molecular sieves; TESOTf / CH2Cl2; toluene / 0.33 h / 20 °C
  • 37
  • [ 22415-91-4 ]
  • [ 116143-85-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 65 mg / 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature
Multi-step reaction with 2 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 65 mg / 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature
  • 38
  • [ 22415-91-4 ]
  • [ 116143-94-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature
Multi-step reaction with 2 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature
  • 39
  • [ 22415-91-4 ]
  • [ 116143-88-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 11.9 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 75.2 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature 3: 125 mg / pyridine / 24 h / Ambient temperature
Multi-step reaction with 4 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 65 mg / 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 75.2 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature 4: 125 mg / pyridine / 24 h / Ambient temperature
Multi-step reaction with 4 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 69.4 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature 4: 125 mg / pyridine / 24 h / Ambient temperature
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 74.6 percent / 16percent methanolic ammonia / methanol / 18 h / Ambient temperature 3: 125 mg / pyridine / 24 h / Ambient temperature
Multi-step reaction with 3 steps 1: 11.9 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 75.2 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature 3: 125 mg / pyridine / 24 h / Ambient temperature
Multi-step reaction with 4 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 65 mg / 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 75.2 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature 4: 125 mg / pyridine / 24 h / Ambient temperature
Multi-step reaction with 4 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 69.4 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature 4: 125 mg / pyridine / 24 h / Ambient temperature
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 74.6 percent / 16percent methanolic ammonia / methanol / 18 h / Ambient temperature 3: 125 mg / pyridine / 24 h / Ambient temperature

  • 40
  • [ 22415-91-4 ]
  • [ 116143-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 11.9 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 228 mg / pyridine
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 65 mg / 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 228 mg / pyridine
Multi-step reaction with 2 steps 1: 11.9 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 228 mg / pyridine
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 65 mg / 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 228 mg / pyridine

  • 41
  • [ 22415-91-4 ]
  • [ 116144-01-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 190 mg / pyridine / 24 h / Ambient temperature
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 190 mg / pyridine / 24 h / Ambient temperature
  • 42
  • [ 22415-91-4 ]
  • [ 116143-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.4 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 50 mg / pyridine / 24 h / 0 °C
  • 43
  • [ 22415-91-4 ]
  • [ 116143-99-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5.4 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 75 mg / pyridine / 24 h / 0 °C
Multi-step reaction with 2 steps 1: 5.4 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 75 mg / pyridine / 24 h / 0 °C
  • 44
  • [ 22415-91-4 ]
  • [ 116143-87-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 11.9 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 75.2 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 65 mg / 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 75.2 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 69.4 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature
Multi-step reaction with 2 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 74.6 percent / 16percent methanolic ammonia / methanol / 18 h / Ambient temperature
Multi-step reaction with 2 steps 1: 11.9 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 75.2 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 65 mg / 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 75.2 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature
Multi-step reaction with 3 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 8 percent 2-propanol-ammonia / propan-2-ol / 18 h / Ambient temperature 3: 69.4 percent / 16 percent methanolic ammonia / methanol / 18 h / Ambient temperature
Multi-step reaction with 2 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 74.6 percent / 16percent methanolic ammonia / methanol / 18 h / Ambient temperature

  • 45
  • [ 22415-91-4 ]
  • [ 116144-03-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 0.7 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 110 mg / pyridine / 24 h / 0 °C
  • 46
  • [ 22415-91-4 ]
  • [ 116143-93-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 215 mg / pyridine / 24 h / Ambient temperature
Multi-step reaction with 2 steps 1: 9.6 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 215 mg / pyridine / 24 h / Ambient temperature
  • 47
  • [ 22415-91-4 ]
  • [ 116144-04-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 0.7 percent / liquid ammonia / CHCl3; dioxane / 100 h / -60 °C 2: 94 mg / sodium acetate / pyridine / 3 h / 100 °C
  • 48
  • [ 22415-91-4 ]
  • [ 6605-40-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane; acetic acid; hydrogen bromide
  • 49
  • [ 821-09-0 ]
  • [ 22415-91-4 ]
  • (2R,3R,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2Hpyran-3,4,5-triyl tribenzoate [ No CAS ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 84% 2: 14% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h; Stage #2: n-Pent-4-enyl alcohol With zinc(II) chloride In dichloromethane at 20℃; for 20h; Further stages.;
  • 50
  • [ 3344-77-2 ]
  • [ 22415-91-4 ]
  • [ 14218-11-2 ]
  • [ 1038587-88-0 ]
  • [ 382607-67-2 ]
YieldReaction ConditionsOperation in experiment
1: 63% 2: 4% 3: 27% With trimethylsilyl bromide; zinc dibromide In dichloromethane at 5 - 20℃; for 24h;
  • 51
  • [ 3344-77-2 ]
  • [ 22415-91-4 ]
  • 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide [ No CAS ]
  • [ 1038587-88-0 ]
  • [ 382607-67-2 ]
YieldReaction ConditionsOperation in experiment
1: 47% 2: 5% 3: 25% With trimethylsilyl iodide; zinc(II) iodide In dichloromethane at 5 - 20℃; for 48h;
  • 52
  • [ 3344-77-2 ]
  • [ 22415-91-4 ]
  • [ 1038587-88-0 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 382607-67-2 ]
YieldReaction ConditionsOperation in experiment
1: 82% 2: 7% 3: 4% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h; Stage #2: 12-bromododecanol With zinc(II) iodide In dichloromethane at 40℃; for 5h; Further stages.;
  • 53
  • [ 3344-77-2 ]
  • [ 22415-91-4 ]
  • [ 1038587-83-5 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 382607-67-2 ]
YieldReaction ConditionsOperation in experiment
1: 62% 2: 18% 3: 7% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h; Stage #2: 12-bromododecanol With N-Bromosuccinimide In dichloromethane at 5 - 10℃; for 6h; Further stages.;
  • 54
  • [ 3344-77-2 ]
  • [ 22415-91-4 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 382607-67-2 ]
YieldReaction ConditionsOperation in experiment
1: 78% 2: 11% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With trimethylsilyl bromide; zinc dibromide at 20℃; for 18h; Stage #2: 12-bromododecanol With zinc dibromide In dichloromethane at 20℃; for 4h; Further stages.;
  • 55
  • [ 60-12-8 ]
  • [ 22415-91-4 ]
  • [ 14218-11-2 ]
  • [ 1038587-89-1 ]
  • [ 1038587-84-6 ]
YieldReaction ConditionsOperation in experiment
1: 68% 2: 16% 3: 2% With trimethylsilyl bromide; zinc dibromide In dichloromethane at 5 - 20℃; for 2h;
  • 56
  • [ 60-12-8 ]
  • [ 22415-91-4 ]
  • 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide [ No CAS ]
  • [ 1038587-89-1 ]
  • [ 1038587-84-6 ]
YieldReaction ConditionsOperation in experiment
1: 73% 2: 9% 3: 5% With trimethylsilyl iodide; zinc(II) iodide In dichloromethane at 5 - 20℃; for 40h;
  • 57
  • [ 60-12-8 ]
  • [ 22415-91-4 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 1038587-84-6 ]
YieldReaction ConditionsOperation in experiment
1: 67% 2: 22% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h; Stage #2: 2-phenylethanol With N-Bromosuccinimide In dichloromethane at 5 - 10℃; for 6h; Further stages.;
  • 58
  • [ 1676-81-9 ]
  • [ 22415-91-4 ]
  • 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide [ No CAS ]
  • [ 1038988-88-3 ]
  • [ 1038587-86-8 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 10% 2: 30% 3: 15% 4: 40% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h; Stage #2: N-benzyloxycarbonyl-L-serine methyl ester With N-Bromosuccinimide In dichloromethane at 5℃; for 4h; Further stages.;
  • 59
  • [ 22415-91-4 ]
  • [ 14218-11-2 ]
  • 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc dibromide In dichloromethane
  • 60
  • [ 22415-91-4 ]
  • 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane
With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h;
With hydrogen iodide In acetic acid
With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane for 16h; 2 1 -lodo-2,3,4,6-Tetra-0-benzoyl-a-D-glucopyranoside (3) 1 -lodo-2,3,4,6-Tetra-0-benzoyl-a-D-glucopyranoside (3) Hexamethyldisilane (0.531 g, 3.63 mmol) in CH2CI2 (10 mL) was added to a solution of a-D-glucose-pentabenzoate(2) (4.10 g, 5.85 mmol) in CH2CI2 (60 mL). To this solution was added Znl2 (0.467 g, 1.46 mmol), followed by l2 (0.921 g, 3.63 mmol) and stirred for 16 hrs. The reaction was quenched by addition of CH2CI2 (40 mL) and an aqueous solution (120 mL) of NaHC03 (1.68 g) and Na2S203 (1.12 g) and then stirring for 10 min until the pinkish colour and milky solution had cleared. The organic phase was separated and washed with brine (50 mL) and the combined aqueous phases extracted with CH2CI2 (2 x 50 mL). The combined organic extracts were dried over MgS0 , filtered and concentrated in vacuo to yield a crude oil of the title compound which was used directly in the next reaction.
With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) chloride In dichloromethane at 20℃; for 16h;

  • 61
  • [ 22415-91-4 ]
  • [ 4064-06-6 ]
  • [ 1038988-91-8 ]
  • [ 70751-54-1 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 67% 2: 7% 3: 20% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h; Stage #2: 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose With N-Bromosuccinimide In dichloromethane at 5 - 10℃; for 6h; Further stages.;
  • 62
  • [ 22415-91-4 ]
  • [ 4064-06-6 ]
  • [ 70751-54-1 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 70% 2: 15% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h; Stage #2: 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose With zinc dibromide In dichloromethane at 20℃; for 30h; Further stages.;
  • 63
  • [ 22415-91-4 ]
  • [ 108-93-0 ]
  • [ 14218-11-2 ]
  • [ 6899-46-3 ]
YieldReaction ConditionsOperation in experiment
1: 32% 2: 54% With trimethylsilyl bromide; zinc dibromide In dichloromethane at 5 - 20℃; for 3h;
  • 64
  • [ 22415-91-4 ]
  • [ 108-93-0 ]
  • 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl iodide [ No CAS ]
  • [ 6899-46-3 ]
YieldReaction ConditionsOperation in experiment
1: 58% 2: 20% With trimethylsilyl iodide; zinc(II) iodide In dichloromethane at 5 - 20℃; for 70h;
  • 65
  • [ 22415-91-4 ]
  • [ 108-93-0 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 6899-46-3 ]
YieldReaction ConditionsOperation in experiment
1: 84% 2: 6% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h; Stage #2: cyclohexanol With zinc(II) chloride In dichloromethane at 20℃; for 6h; Further stages.;
  • 66
  • [ 22415-91-4 ]
  • [ 108-93-0 ]
  • [ 6899-46-3 ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose With 1,1,1,2,2,2-hexamethyldisilane; iodine; zinc(II) iodide In dichloromethane at 20℃; for 6h; Stage #2: cyclohexanol With N-Bromosuccinimide In dichloromethane at 5℃; for 3h; Further stages.;
  • 67
  • [ 2280-44-6 ]
  • [ 98-88-4 ]
  • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose [ No CAS ]
  • [ 22415-91-4 ]
YieldReaction ConditionsOperation in experiment
In pyridine at 20℃; for 12h;
With pyridine at 0 - 20℃; optical yield given as %de;
23.077 % de With pyridine at 0 - 20℃; Overall yield = 79 %; Overall yield = 30.68 g; stereoselective reaction; D-Glucopyranose pentabenzoate Benzoyl chloride (48.0 mL, 34.4 mmol) was added dropwise to a solution of D-glucose (10.0 g, 55.5 mmol) in pyridine (120 mL) at 0 °C. The reaction mixture was allowed to warm to room temp, stirring overnight, before it was diluted with EtOAc (300 mL), and washed with 1.0 M HCl, water and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Recrystallisation from acetone:water gave the title compound (30.68 g, 43.78 mmol, 79%) as a mixture of anomers (α:β = 1.6:1). Rf 0.44 (cyclohexane-EtOAc 1:1); 1H NMR (500 MHz, CDCl3) δ 8.20-8.15 (overlapping signals, 2H, Ar-H), 8.14-8.10 (m, 1H, Ar-H), 8.06-8.01 (overlapping signals, 5H, Ar-H), 7.97-7.84 (overlapping signals, 12H, Ar-H), 7.68 (d, J = 1.5 Hz, 1H, Ar-H), 7.64-7.58 (m, 1H, Ar-H), 7.59-7.28 (overlapping signals, 28H, Ar-H), 6.86 (d, J = 3.7 Hz, 1H, H-1α), 6.32 (t, J = 10.3 Hz, 1H, H-3α), 6.30 (d, J = 5.4 Hz, 1H, H-1β), 6.04 (t, J = 9.5 Hz, 1H, H-3β), 5.89-5.81 (overlapping signals, 3H, H-2β, H-4β and H-4α), 5.69 (dd, J = 10.3, 3.7 Hz, 1H, H-2α), 4.69-4.60 (overlapping signals, 3H, H-5α, H-6aα and H-6aβ), 4.54-4.47 (overlapping signals, 2H, H-6bα and H-6bβ), 4.41 (ddd, J = 9.8, 4.8, 3.0 Hz, 1H, H-5β); 13C NMR (126 MHz, CDCl3) δ 166.1, 166.1, 165.9, 165.7, 165.3, 165.1, 165.1, 164.6, 164.4 (each C=O), 133.9, 133.8, 133.6, 133.5, 133.5, 133.4, 133.3, 133.1, 133.1, 130.2, 130.2, 130.0, 129.9, 129.8, 129.8, 129.8, 129.8, 129.7, 129.5, 129.0, 128.8, 128.8, 128.7, 128.7, 128.5, 128.5, 128.5, 128.4, 128.4, 128.4, 128.3 (Ar-C and CH), 92.7 (C-1β), 90.0 (C-1α), 73.2 (C-5β), 72.8 (C-3β), 70.8 (C-2β), 70.5, 70.5, 70.4 (C-2α, C-3α and C-5α), 69.1 (C-5β), 68.8 (C-4α), 62.4 (C-6β); IR (ATR) cm-1: 3065, 1728, 1451, 1262, 1092, 1068, 1020, 707; ESI-HRMS calcd for C41H36NO11 718.2288, found m/z 718.2253 [M+NH4]+.
71.429 % de With pyridine; dmap at 0 - 20℃; Inert atmosphere; Overall yield = 99 percent; Overall yield = 953 mg;

  • 68
  • [ 22415-91-4 ]
  • [ 165877-99-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide In dichloromethane; acetic acid at 20℃;
With hydrogen bromide; acetic acid In dichloromethane at 0 - 20℃;
  • 69
  • [ 22415-91-4 ]
  • [ 66530-18-5 ]
  • [ 64768-20-3 ]
YieldReaction ConditionsOperation in experiment
With ethanol; methylamine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; optical yield given as %de;
60 % de With methylamine In tetrahydrofuran; methanol at 20℃; for 6h; Inert atmosphere; Overall yield = 68 %; Overall yield = 0.76 g; 2,3,4,6-Tetra-O-benzoyl-α/β-D-glucopyranose (41) MeNH2 in THF (2.0 M; 5.2 mL, 10.2 mmol) was added to pentabenzoate 40 (1.3 g, 1.86 mmol) in THFand MeOH (5:1, 6 mL) and the mixture stirred for 6 h at room temperature. The mixture was rotaryevaporated and chromatographed (30% EtOAc in hexanes) to yield pyranose 41 (0.76 g, 68%) as acolorless solid as a 4:1 mixture of α and β anomers
  • 70
  • [ 192376-76-4 ]
  • [ 22415-91-4 ]
  • [ 1231608-85-7 ]
  • [ 1231608-82-4 ]
YieldReaction ConditionsOperation in experiment
1: 0.026 g 2: 0.045 g With boron trifluoride diethyl etherate In dichloromethane at 0℃; Inert atmosphere; Reflux;
  • 71
  • [ 22415-91-4 ]
  • 5-(N-benzyloxycarbonyl)aminopentyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogen bromide; acetic acid / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: caesium carbonate / dichloromethane / 12 h / 20 °C / Inert atmosphere 3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere 3.2: 12 h / 10 - 20 °C / Inert atmosphere
  • 72
  • [ 22415-91-4 ]
  • [ 149707-75-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogen bromide; acetic acid / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: caesium carbonate / dichloromethane / 12 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: methylamine / tetrahydrofuran / 2 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 4 h / 20 °C
Multi-step reaction with 2 steps 1: hydrazinium monoacetate / N,N-dimethyl-formamide / 30 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C
  • 73
  • [ 22415-91-4 ]
  • [ 382607-66-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 17 h / Inert atmosphere; Molecular sieve
Multi-step reaction with 2 steps 1: iodine; 1,1,1,2,2,2-hexamethyldisilane; zinc(II) chloride / dichloromethane / 16 h / 20 °C 2: zinc(II) chloride / dichloromethane / Molecular sieve
  • 74
  • [ 22415-91-4 ]
  • 10-(tert-butyldiphenylsilyloxy)decyl-tetra-O-benzoyl-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 8 h / Molecular sieve
  • 75
  • [ 22415-91-4 ]
  • 10-hydroxydecyl-tetra-O-benzoyl-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 8 h / Molecular sieve 3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 36 h
  • 76
  • [ 22415-91-4 ]
  • 10-(tetra-O-benzoyl-β-D-glucopyranos-1-yl)-decanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 8 h / Molecular sieve 3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 36 h 4: Dess-Martin periodane / dichloromethane / 1.5 h
  • 77
  • [ 22415-91-4 ]
  • 10-(tetra-O-benzoyl-β-D-glucopyranos-1-yl)-decanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 8 h / Molecular sieve 3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 36 h 4: Dess-Martin periodane / dichloromethane / 1.5 h 5: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / <i>tert</i>-butyl alcohol
  • 78
  • [ 22415-91-4 ]
  • 10-(tetra-O-benzoyl-β-D-glucopyranos-1-yl)-decanoyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 8 h / Molecular sieve 3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 36 h 4: Dess-Martin periodane / dichloromethane / 1.5 h 5: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / <i>tert</i>-butyl alcohol 6: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere
  • 79
  • [ 22415-91-4 ]
  • C45H79N5O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 8 h / Molecular sieve 3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 36 h 4: Dess-Martin periodane / dichloromethane / 1.5 h 5: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / <i>tert</i>-butyl alcohol 6: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1 h / 0 °C / Inert atmosphere 7: dmap; triethylamine / tetrahydrofuran / 1.5 h 8: sodium methylate / methanol / 1 h / Inert atmosphere
  • 80
  • [ 22415-91-4 ]
  • C66H90N4O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 17 h / Inert atmosphere; Molecular sieve 3: potassium carbonate / acetonitrile / 72 h / 60 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: iodine; 1,1,1,2,2,2-hexamethyldisilane; zinc(II) chloride / dichloromethane / 16 h / 20 °C 2: zinc(II) chloride / dichloromethane / Molecular sieve 3: potassium carbonate / acetonitrile / 16 h / 60 °C
  • 81
  • [ 22415-91-4 ]
  • C38H74N4O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 17 h / Inert atmosphere; Molecular sieve 3: potassium carbonate / acetonitrile / 72 h / 60 °C / Inert atmosphere 4: sodium methylate / methanol / 0.5 h
  • 82
  • [ 22415-91-4 ]
  • C48H86N4O12S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 17 h / Inert atmosphere; Molecular sieve 3: potassium carbonate / acetonitrile / 72 h / 60 °C / Inert atmosphere 4: sodium methylate / methanol / 0.5 h 5: potassium carbonate / acetonitrile / 24 h / 60 °C / Inert atmosphere
  • 83
  • [ 22415-91-4 ]
  • C46H86N4O10S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 17 h / Inert atmosphere; Molecular sieve 3: potassium carbonate / acetonitrile / 72 h / 60 °C / Inert atmosphere 4: sodium methylate / methanol / 0.5 h 5: potassium carbonate / acetonitrile / 24 h / 60 °C / Inert atmosphere 6: acetonitrile / 2 h / Reflux
  • 84
  • [ 22415-91-4 ]
  • C56H109N5O12S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 17 h / Inert atmosphere; Molecular sieve 3: potassium carbonate / acetonitrile / 72 h / 60 °C / Inert atmosphere 4: sodium methylate / methanol / 0.5 h 5: potassium carbonate / acetonitrile / 24 h / 60 °C / Inert atmosphere 6: acetonitrile / 2 h / Reflux
  • 85
  • [ 22415-91-4 ]
  • C43H85N5O10S2*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1,1,1,2,2,2-hexamethyldisilane; zinc(II) iodide; iodine / dichloromethane / 16 h 2: zinc(II) chloride / dichloromethane / 17 h / Inert atmosphere; Molecular sieve 3: potassium carbonate / acetonitrile / 72 h / 60 °C / Inert atmosphere 4: sodium methylate / methanol / 0.5 h 5: potassium carbonate / acetonitrile / 24 h / 60 °C / Inert atmosphere 6: acetonitrile / 2 h / Reflux 7: hydrogenchloride / ethyl acetate / 2 h
Same Skeleton Products
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