1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose
• CAS No.: 220099-50-3
• Molecular Formula: C₄₀H₄₄O₉
• Molecular Weight: 668.784

Synonyms:1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose

Chemical Property of 1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose

Chemical Property:

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Technology Process of 1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose

There total 2 articles about 1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-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: 82.6%

1,6:2,3-dianhydro-4-O-(2,3,5,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-mannopyranose (107952-48-7) → 1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose (220099-50-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 4h; Heating;

DOI:10.1016/S0040-4039(98)02234-5

Reference yield:

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate (90357-89-4) → 1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose (220099-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: TBDMSOTf, NaHCO₃ / CH₂Cl₂ / 0.25 h / -30 °C

2: 82.6 percent / LAH / diethyl ether / 4 h / Heating

With lithium aluminium tetrahydride; t-butyldimethylsiyl triflate; sodium hydrogencarbonate; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(98)02234-5

Reference yield: 88.1%

benzyl bromide (100-39-0) + 1,6-anhydro-2-deoxy-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose (220099-50-3) → (1R,2S,3R,5R)-3-Benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6,8-dioxa-bicyclo[3.2.1]octane (220099-51-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 4h; Ambient temperature;

DOI:10.1016/S0040-4039(98)02234-5

upstream raw materials:

1,6:2,3-dianhydro-4-O-(2,3,5,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-mannopyranose

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate

Downstream raw materials:

(1R,2S,3R,5R)-3-Benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6,8-dioxa-bicyclo[3.2.1]octane

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