S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside
• CAS No.: 1334540-18-9
• Molecular Formula: C₅₁H₅₄O₉S
• Molecular Weight: 843.05

Synonyms:S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

Chemical Property of S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside

There total 15 articles about S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-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: 79.0%

S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-1-thio-β-D-glucopyranoside (1334540-47-4) + levulinic anhydride (40608-06-8) → S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside (1334540-18-9)

Guidance literature:

With pyridine; In dichloromethane; for 72h;

DOI:10.1039/c1cc13614c

Reference yield:

β-D-glucose pentaacetate (604-69-3) → S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside (1334540-18-9)

Guidance literature:

Multi-step reaction with 9 steps

1: boron trifluoride diethyl etherate / dichloromethane

2: sodium methylate / methanol / 20 °C

3: camphor-10-sulfonic acid / acetonitrile / 2.5 h / 20 °C / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 0 °C

5: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

7: pyridine / dichloromethane

8: trifluorormethanesulfonic acid; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid / dichloromethane / 3 h / -78 °C / Molecular sieve

9: pyridine / dichloromethane / 72 h

With pyridine; 1H-imidazole; trifluorormethanesulfonic acid; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c1cc13614c

Reference yield:

S-(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-1-thio-?-D-glucopyranoside (1334540-41-8) → S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside (1334540-18-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane

2: trifluorormethanesulfonic acid; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid / dichloromethane / 3 h / -78 °C / Molecular sieve

3: pyridine / dichloromethane / 72 h

With pyridine; trifluorormethanesulfonic acid; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; In dichloromethane;

DOI:10.1039/c1cc13614c

upstream raw materials:

S-(2-methyl-5-tert-butylphenyl) 4,6-O-benzylidene-2-O-benzyl-1-thio-?-D-glucopyranoside

S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-1-thio-β-D-glucopyranoside

levulinic anhydride

(2-methyl-5-tert-butylphenyl) 1-thio-β-D-glucopyranoside

Downstream raw materials:

2,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-4-O-levulinoyl-α-D-glucopyranosyl-(1→2)-(N-(benzyl)-N-benzyloxycarbonyl-5-amino-pentyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside

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