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

Base Information

• Chemical Name: octyl (5a-carba-β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• CAS No.: 198202-08-3
• Molecular Formula: C₂₃H₄₃NO₁₀
• Molecular Weight: 493.595

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 26 articles about octyl (5a-carba-β-D-galactopyranosyl)-(1->4)-2-acetamido-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: 91.0%

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 (198202-23-2) → octyl (5a-carba-β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside (198202-08-3)

Guidance literature:

With sodium methylate; In methanol; for 3.5h; Ambient temperature;

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

Reference yield:

octanol (111-87-5) → octyl (5a-carba-β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside (198202-08-3)

Guidance literature:

Multi-step reaction with 16 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

13: 1.) NaAc / 1.) aq. DMF, 2 d, 120 deg C; 2.) pyridine

14: H₂ / Pd/C / ethanol / 2 h / Ambient temperature

15: 13 mg / pyridine

16: 91 percent / sodium methoxide / methanol / 3.5 h / Ambient temperature

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

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (70749-28-9) → octyl (5a-carba-β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside (198202-08-3)

Guidance literature:

Multi-step reaction with 16 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

13: 1.) NaAc / 1.) aq. DMF, 2 d, 120 deg C; 2.) pyridine

14: H₂ / Pd/C / ethanol / 2 h / Ambient temperature

15: 13 mg / pyridine

16: 91 percent / sodium methoxide / methanol / 3.5 h / Ambient temperature

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

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

octanol

D-glucosamine hydrochloride

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

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