O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Base Information

• Chemical Name: O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose
• CAS No.: 104139-77-7
• Molecular Formula: C₃₆H₃₆ClN₃O₁₂
• Molecular Weight: 738.148

Synonyms:

Chemical Property of O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

There total 17 articles about O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-18-6) → O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (104139-77-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) dibutyltin oxide; 2.) tetrabutylammonium iodide / 1.) toluene, 15 h, reflux; 2.) 5 h, 100 deg C

2: 98 percent / pyridine / 5 h / Ambient temperature

3: 88 percent / 1 M tetrabutylammonium fluoride / acetonitrile; H₂O; tetrahydrofuran / 10 h / Ambient temperature

4: 91.5 percent / CHCl₃; pyridine / 96 h / Ambient temperature

5: 94.6 percent / 60 percent NaH / tetrahydrofuran; dimethylformamide; paraffin / 0.08 h / Ambient temperature

6: 88.5 percent / sodium azide, ammonium chloride / dimethylformamide; H₂O / 40 h / 110 °C

7: 91.4 percent / 60 percent NaH, tetrabutylammonium iodide / paraffin; tetrahydrofuran / 0.83 h / Ambient temperature

8: 85.6 percent / cupric chloride dihydrate / tetrahydrofuran; ethanol / 1.5 h / Heating

9: 1.) bis(tributyltin)oxide / 1.) toluene, 3 h, reflux; 2.) 3 h, 80 deg C

10: 95.9 percent / NaI / acetone / 14 h / Heating

11: 88.1 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 18 h / Heating

12: 1.) methyl iodide, tetrabutylammonium borohydride; 2.) 30 percent H₂O₂, sat. NaHCO₃ / 1.) CH₂Cl₂, 30 min, RT; 2.) water, CH₂Cl₂, 50 min, RT

13: 1.) pyridine, 100 deg C, 12 h; 2.) pyridine, 0-5 deg C, 2 h

14: CrO₃, 3.5 M H₂SO₄ / acetone / 3 h / Ambient temperature

15: diethyl ether; CH₂Cl₂

With pyridine; chromium(VI) oxide; sodium azide; sulfuric acid; ammonium chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; tetrabutylammonium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(tri-n-butyltin)oxide; sodium iodide; copper dichloride; methyl iodide; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile; paraffin;

DOI:10.1016/S0008-6215(00)90842-5

Reference yield:

O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose (115997-40-5) → O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (104139-77-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 88.5 percent / sodium azide, ammonium chloride / dimethylformamide; H₂O / 40 h / 110 °C

2: 91.4 percent / 60 percent NaH, tetrabutylammonium iodide / paraffin; tetrahydrofuran / 0.83 h / Ambient temperature

3: 85.6 percent / cupric chloride dihydrate / tetrahydrofuran; ethanol / 1.5 h / Heating

4: 1.) bis(tributyltin)oxide / 1.) toluene, 3 h, reflux; 2.) 3 h, 80 deg C

5: 95.9 percent / NaI / acetone / 14 h / Heating

6: 88.1 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 18 h / Heating

7: 1.) methyl iodide, tetrabutylammonium borohydride; 2.) 30 percent H₂O₂, sat. NaHCO₃ / 1.) CH₂Cl₂, 30 min, RT; 2.) water, CH₂Cl₂, 50 min, RT

8: 1.) pyridine, 100 deg C, 12 h; 2.) pyridine, 0-5 deg C, 2 h

9: CrO₃, 3.5 M H₂SO₄ / acetone / 3 h / Ambient temperature

10: diethyl ether; CH₂Cl₂

With chromium(VI) oxide; sodium azide; sulfuric acid; ammonium chloride; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; tetrabutylammonium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(tri-n-butyltin)oxide; sodium iodide; copper dichloride; methyl iodide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; paraffin;

DOI:10.1016/S0008-6215(00)90842-5

Reference yield:

O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (104139-74-4) → O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (104139-77-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) methyl iodide, tetrabutylammonium borohydride; 2.) 30 percent H₂O₂, sat. NaHCO₃ / 1.) CH₂Cl₂, 30 min, RT; 2.) water, CH₂Cl₂, 50 min, RT

2: 1.) pyridine, 100 deg C, 12 h; 2.) pyridine, 0-5 deg C, 2 h

3: CrO₃, 3.5 M H₂SO₄ / acetone / 3 h / Ambient temperature

4: diethyl ether; CH₂Cl₂

With chromium(VI) oxide; sulfuric acid; dihydrogen peroxide; sodium hydrogencarbonate; tetrabutylammonium borohydride; methyl iodide; In diethyl ether; dichloromethane; acetone;

DOI:10.1016/S0008-6215(00)90842-5

upstream raw materials:

diazomethane

(2R,3S,4S,5R,6R)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid

benzyl bromide

1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

Downstream raw materials:

O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R)-2-Acetoxymethyl-5-azido-4-benzyloxy-6-bromo-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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