octyl (2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: octyl (2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 198202-28-7
• Molecular Formula: C₄₈H₆₇NO₁₅S₂
• Molecular Weight: 962.19

Synonyms:

Chemical Property of octyl (2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of octyl (2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 17 articles about octyl (2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-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 (2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (198202-28-7)

Guidance literature:

Multi-step reaction with 15 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: 1.) N,N-diisopropylethylamine / 1.) dichloromethane, RT, 30 min; 2.) 4 h, 40 deg C

6: H₂ / Pd/C / ethanol; ethyl acetate / 1.5 h / Ambient temperature

7: NaH / dimethylformamide / 2 h / Ambient temperature

8: 94 percent / conc. HCl / tetrahydrofuran / 4 h / Ambient temperature

9: 48 percent / NaH, 15-crown-5 ether / dimethylformamide / 96 h / 80 °C

10: 71 percent / PCC, molecular sieves (4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

11: 81 percent / DBU / toluene / 2.5 h / 60 °C

12: borane-dimethyl sulfide / tetrahydrofuran / 13 h / Ambient temperature

13: 61 percent / pyridine / Ambient temperature

14: aq. acetic acid / 1 h / 70 °C

15: 114 mg / pyridine / 3 h / Ambient temperature

With hydrogenchloride; potassium sulfate; 15-crown-5; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; sodium methylate; iron(III) chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene;

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 (2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (198202-28-7)

Guidance literature:

Multi-step reaction with 16 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: 1.) N,N-diisopropylethylamine / 1.) dichloromethane, RT, 30 min; 2.) 4 h, 40 deg C

7: H₂ / Pd/C / ethanol; ethyl acetate / 1.5 h / Ambient temperature

8: NaH / dimethylformamide / 2 h / Ambient temperature

9: 94 percent / conc. HCl / tetrahydrofuran / 4 h / Ambient temperature

10: 48 percent / NaH, 15-crown-5 ether / dimethylformamide / 96 h / 80 °C

11: 71 percent / PCC, molecular sieves (4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

12: 81 percent / DBU / toluene / 2.5 h / 60 °C

13: borane-dimethyl sulfide / tetrahydrofuran / 13 h / Ambient temperature

14: 61 percent / pyridine / Ambient temperature

15: aq. acetic acid / 1 h / 70 °C

16: 114 mg / pyridine / 3 h / Ambient temperature

With hydrogenchloride; potassium sulfate; 15-crown-5; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; sodium methylate; iron(III) chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene;

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 (2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (198202-28-7)

Guidance literature:

Multi-step reaction with 15 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: 1.) N,N-diisopropylethylamine / 1.) dichloromethane, RT, 30 min; 2.) 4 h, 40 deg C

6: H₂ / Pd/C / ethanol; ethyl acetate / 1.5 h / Ambient temperature

7: NaH / dimethylformamide / 2 h / Ambient temperature

8: 94 percent / conc. HCl / tetrahydrofuran / 4 h / Ambient temperature

9: 48 percent / NaH, 15-crown-5 ether / dimethylformamide / 96 h / 80 °C

10: 71 percent / PCC, molecular sieves (4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

11: 81 percent / DBU / toluene / 2.5 h / 60 °C

12: borane-dimethyl sulfide / tetrahydrofuran / 13 h / Ambient temperature

13: 61 percent / pyridine / Ambient temperature

14: aq. acetic acid / 1 h / 70 °C

15: 114 mg / pyridine / 3 h / Ambient temperature

With hydrogenchloride; potassium sulfate; 15-crown-5; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; sodium methylate; iron(III) chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

methanesulfonyl chloride

octanol

D-glucosamine hydrochloride

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

Downstream raw materials:

octyl (2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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