ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside
• CAS No.: 1415663-26-1
• Molecular Formula: C₂₄H₃₁NO₄S
• Molecular Weight: 429.58
• Mol file: 1415663-26-1.mol

Synonyms:ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside

There total 14 articles about ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-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: 74.0%

C17H25NO4S (1415663-27-2) + benzyl bromide (100-39-0) → ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside (1415663-26-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield: 71.0%

1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose (1415663-22-7) + ethanethiol (75-08-1) → ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside (1415663-26-1) + C17H25NO4S (1415663-27-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 30 ℃; for 48h; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.bmcl.2012.10.064

Reference yield:

methyl 2,3-di-O-benzoyl-4-O-benzyl-α-D-glucopyranoside (89539-31-1) → ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside (1415663-26-1)

Guidance literature:

Multi-step reaction with 10 steps

1: triphenylphosphine; carbon tetrabromide / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere

2: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 3.5 h / 20 - 80 °C / Inert atmosphere

3: sodium methylate / dichloromethane; methanol / 10 h / pH 10

4: pyridine; p-toluenesulfonyl chloride; dmap / 20 - 80 °C / Inert atmosphere

5: sodium methylate / dichloromethane; methanol / 48 h / 0 - 5 °C / Inert atmosphere

6: water / 6 h / Inert atmosphere; Heating

7: pyridine / 3 h / 0 - 20 °C / Inert atmosphere

8: acetic acid; sulfuric acid / 48 h / Inert atmosphere

9: boron trifluoride diethyl etherate / dichloromethane / 48 h / 30 °C / Inert atmosphere; Molecular sieve

10: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; sulfuric acid; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; acetic acid; p-toluenesulfonyl chloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2012.10.064

upstream raw materials:

benzaldehyde dimethyl acetal

methyl 2,3-di-O-benzoyl-4-O-benzyl-α-D-glucopyranoside

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside

methyl 2,3-di-O-benzoyl-4-O-benzyl-6-deoxy-α-D-glucopyranoside

Downstream raw materials:

5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A?11,12-cyclic carbonate

5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate