octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside

Base Information

• Chemical Name: octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside
• CAS No.: 222191-79-9
• Molecular Formula: C₃₅H₅₆N₂O₁₅
• Molecular Weight: 744.834

Synonyms:octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside

Chemical Property of octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside

There total 16 articles about octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside 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:

octanol (111-87-5) → octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside (222191-79-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 44 percent / potassium sulfate, ferric chloride / CH₂Cl₂ / 16 h / Ambient temperature

2: NaOMe / methanol / 1 h / Ambient temperature

3: 88 percent / zinc chloride / 3 h / Ambient temperature

4: 82 percent / NaH / dimethylformamide / 6 h / Ambient temperature

5: 68 percent / molecular sieves (4 Angstroem), sodium cyanoborohydride / tetrahydrofuran / 0.5 h / Ambient temperature

6: 1.) Ac₂O; 2.) L-selectride / 1.) DMSO, RT; 2.) THF, 7 h, -15 deg C

7: 87 percent / pyridine / 2.5 h / Ambient temperature

8: 96 percent / NaN₃ / dimethylformamide; H₂O / 48 h / 120 °C

9: 80 percent / H₂, HCl / Pd/C / ethanol; ethyl acetate / Ambient temperature

10: 38 percent / propan-2-ol / 504 h / 120 °C

11: 26 mg / aq. acetic acid / 2 h / 60 °C

12: H₂, HCl / Pd/C / ethanol / 2 h

13: pyridine

With hydrogenchloride; potassium sulfate; sodium azide; 4 A molecular sieve; hydrogen; sodium methylate; acetic anhydride; iron(III) chloride; L-Selectride; sodium hydride; sodium cyanoborohydride; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1002/(SICI)1099-0690(199903)1999:3<631::AID-EJOC631>3.0.CO;2-6

Reference yield:

D-glucosamine hydrochloride (14131-63-6) → octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside (222191-79-9)

Guidance literature:

Multi-step reaction with 14 steps

1: NaOMe / pyridine / Ambient temperature

2: 44 percent / potassium sulfate, ferric chloride / CH₂Cl₂ / 16 h / Ambient temperature

3: NaOMe / methanol / 1 h / Ambient temperature

4: 88 percent / zinc chloride / 3 h / Ambient temperature

5: 82 percent / NaH / dimethylformamide / 6 h / Ambient temperature

6: 68 percent / molecular sieves (4 Angstroem), sodium cyanoborohydride / tetrahydrofuran / 0.5 h / Ambient temperature

7: 1.) Ac₂O; 2.) L-selectride / 1.) DMSO, RT; 2.) THF, 7 h, -15 deg C

8: 87 percent / pyridine / 2.5 h / Ambient temperature

9: 96 percent / NaN₃ / dimethylformamide; H₂O / 48 h / 120 °C

10: 80 percent / H₂, HCl / Pd/C / ethanol; ethyl acetate / Ambient temperature

11: 38 percent / propan-2-ol / 504 h / 120 °C

12: 26 mg / aq. acetic acid / 2 h / 60 °C

13: H₂, HCl / Pd/C / ethanol / 2 h

14: pyridine

With hydrogenchloride; potassium sulfate; sodium azide; 4 A molecular sieve; hydrogen; sodium methylate; acetic anhydride; iron(III) chloride; L-Selectride; sodium hydride; sodium cyanoborohydride; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1002/(SICI)1099-0690(199903)1999:3<631::AID-EJOC631>3.0.CO;2-6

Reference yield:

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (70749-28-9) → octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside (222191-79-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 44 percent / potassium sulfate, ferric chloride / CH₂Cl₂ / 16 h / Ambient temperature

2: NaOMe / methanol / 1 h / Ambient temperature

3: 88 percent / zinc chloride / 3 h / Ambient temperature

4: 82 percent / NaH / dimethylformamide / 6 h / Ambient temperature

5: 68 percent / molecular sieves (4 Angstroem), sodium cyanoborohydride / tetrahydrofuran / 0.5 h / Ambient temperature

6: 1.) Ac₂O; 2.) L-selectride / 1.) DMSO, RT; 2.) THF, 7 h, -15 deg C

7: 87 percent / pyridine / 2.5 h / Ambient temperature

8: 96 percent / NaN₃ / dimethylformamide; H₂O / 48 h / 120 °C

9: 80 percent / H₂, HCl / Pd/C / ethanol; ethyl acetate / Ambient temperature

10: 38 percent / propan-2-ol / 504 h / 120 °C

11: 26 mg / aq. acetic acid / 2 h / 60 °C

12: H₂, HCl / Pd/C / ethanol / 2 h

13: pyridine

With hydrogenchloride; potassium sulfate; sodium azide; 4 A molecular sieve; hydrogen; sodium methylate; acetic anhydride; iron(III) chloride; L-Selectride; sodium hydride; sodium cyanoborohydride; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1002/(SICI)1099-0690(199903)1999:3<631::AID-EJOC631>3.0.CO;2-6

upstream raw materials:

acetic anhydride

octanol

D-glucosamine hydrochloride

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

Downstream raw materials:

octyl 2-acetamido-4-(1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-2,4-dideoxy-β-D-glucopyranoside

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