methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside
• CAS No.: 1184705-45-0
• Molecular Formula: C₄₂H₄₂O₆S₂
• Molecular Weight: 706.924

Synonyms:methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside

Chemical Property of methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside

There total 6 articles about methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-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: 89.0%

carbon disulfide (75-15-0,12122-00-8) + methyl 3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside (1184705-42-7) + methyl iodide (74-88-4) → methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside (1184705-45-0)

Guidance literature:

carbon disulfide; methyl 3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside; With 1H-imidazole; sodium hydride; In tetrahydrofuran; at 20 ℃; for 3.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/ejoc.200900310

Reference yield:

trityl chloride (76-83-5) → methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside (1184705-45-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 3 h / 90 °C

2.1: tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide / acetonitrile / 16 h / 82 °C / Soxhlet apparatus; Molecular sieve

3.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 0 °C

3.2: 0 - 20 °C

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

5.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

5.2: 1.5 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; water; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.200900310

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside (1184705-45-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 3 h / 90 °C

2.1: tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide / acetonitrile / 16 h / 82 °C / Soxhlet apparatus; Molecular sieve

3.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 0 °C

3.2: 0 - 20 °C

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

5.1: 1H-imidazole; sodium hydride / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

5.2: 1.5 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; water; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.200900310

upstream raw materials:

carbon disulfide

methyl 3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside

methyl iodide

trityl chloride

Downstream raw materials:

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

(3R,4R,6R)-6-(benzylamino)-3,4-bis(benzyloxy)nona-1,8-diene

(3R,4R,6S)-6-(benzylamino)-3,4-bis(benzyloxy)nona-1,8-diene

(3R,4R,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene

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