1,1⁶-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis(methoxymethoxy)phenyl>-2,3,4,6,-tetra-O-benzyl-α-D-glucopyranose

Base Information

• Chemical Name: 1,1⁶-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis(methoxymethoxy)phenyl>-2,3,4,6,-tetra-O-benzyl-α-D-glucopyranose
• CAS No.: 125568-58-3
• Molecular Formula: C₄₅H₄₈O₁₀
• Molecular Weight: 748.87

Synonyms:1,1⁶-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis(methoxymethoxy)phenyl>-2,3,4,6,-tetra-O-benzyl-α-D-glucopyranose

Chemical Property of 1,1⁶-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis(methoxymethoxy)phenyl>-2,3,4,6,-tetra-O-benzyl-α-D-glucopyranose

Chemical Property:

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Technology Process of 1,1⁶-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis(methoxymethoxy)phenyl>-2,3,4,6,-tetra-O-benzyl-α-D-glucopyranose

There total 1 articles about 1,1⁶-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis(methoxymethoxy)phenyl>-2,3,4,6,-tetra-O-benzyl-α-D-glucopyranose 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:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + (2-bromo-3,5-bis(methoxymethoxy)phenyl)methanol (79834-15-4) → <4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone (62641-00-3) + 1,16-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis(methoxymethoxy)phenyl>-2,3,4,6,-tetra-O-benzyl-β-D-glucopyranose (125639-32-9) + 1,16-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis(methoxymethoxy)phenyl>-2,3,4,6,-tetra-O-benzyl-α-D-glucopyranose (125568-58-3)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -78 deg C, 30 min, 2a.) -78 deg C, 7 h, 2b.) -55 deg C, 12 h;

Reference yield:

1,16-anhydro-1-C-<6-(hydroxymethyl)-2,4-bis(methoxymethoxy)phenyl>-2,3,4,6,-tetra-O-benzyl-α-D-glucopyranose (125568-58-3) → C24H28O10 (125568-61-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / H₂ / 10percent Pd-C / ethanol / 5.5 h / 45 °C / 760 Torr

2: 60 percent / p-toluenesulfonic acid / dimethylformamide / 1.5 h / 22 - 90 °C / 14 Torr

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

upstream raw materials:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

(2-bromo-3,5-bis(methoxymethoxy)phenyl)methanol

Downstream raw materials:

C₂₄H₂₈O₁₀

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