octyl <2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-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->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 198202-21-0
• 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->4)-2-acetamido-3,6-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->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 21 articles about octyl <2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-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:

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->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (198202-21-0)

Guidance literature:

Multi-step reaction with 12 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: 66 percent / NaH, 15-crown-5 ether / dimethylformamide / 26 h / 70 °C

7: 75 percent / PCC, molecular sieves (4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

8: 79 percent / DBU / toluene / 2.5 h / 60 °C

9: 40 mg / borane-dimethyl sulfide / tetrahydrofuran / 3.5 h / Ambient temperature

10: 15 percent / pyridine / Ambient temperature

11: aq. acetic acid / 5 h / 70 °C

12: 52 mg / pyridine / 3 h / Ambient temperature

With potassium sulfate; 15-crown-5; dimethylsulfide borane complex; 4 A molecular sieve; sodium methylate; iron(III) chloride; sodium hydride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; zinc(II) chloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetic acid; 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->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (198202-21-0)

Guidance literature:

Multi-step reaction with 13 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: 66 percent / NaH, 15-crown-5 ether / dimethylformamide / 26 h / 70 °C

8: 75 percent / PCC, molecular sieves (4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

9: 79 percent / DBU / toluene / 2.5 h / 60 °C

10: 40 mg / borane-dimethyl sulfide / tetrahydrofuran / 3.5 h / Ambient temperature

11: 15 percent / pyridine / Ambient temperature

12: aq. acetic acid / 5 h / 70 °C

13: 52 mg / pyridine / 3 h / Ambient temperature

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

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

Reference yield:

octyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside (147126-58-7,383417-49-0) → octyl <2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (198202-21-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / zinc chloride / 3 h / Ambient temperature

2: 82 percent / NaH / dimethylformamide / 6 h / Ambient temperature

3: 68 percent / molecular sieves (4 Angstroem), sodium cyanoborohydride / tetrahydrofuran / 0.5 h / Ambient temperature

4: 66 percent / NaH, 15-crown-5 ether / dimethylformamide / 26 h / 70 °C

5: 75 percent / PCC, molecular sieves (4 Angstroem) / CH₂Cl₂ / 1 h / Ambient temperature

6: 79 percent / DBU / toluene / 2.5 h / 60 °C

7: 40 mg / borane-dimethyl sulfide / tetrahydrofuran / 3.5 h / Ambient temperature

8: 15 percent / pyridine / Ambient temperature

9: aq. acetic acid / 5 h / 70 °C

10: 52 mg / pyridine / 3 h / Ambient temperature

With 15-crown-5; dimethylsulfide borane complex; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; zinc(II) chloride; In tetrahydrofuran; pyridine; dichloromethane; acetic acid; 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

D-glucosamine hydrochloride

benzaldehyde

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

Downstream raw materials:

octyl (5a-carba-β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside

octyl <2,3,4,6-tetra-O-acetyl-5a-carba-β-D-galactopyranosyl>-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside

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

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