(6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose

Base Information

• Chemical Name: (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose
• CAS No.: 201660-34-6
• Molecular Formula: C₂₅H₃₂O₁₀
• Molecular Weight: 492.523
• Mol file: 201660-34-6.mol

Synonyms:(6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose

Chemical Property of (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose

There total 1 articles about (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose 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%

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) + 1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose (123823-24-5) → (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose (201660-34-6)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0957-4166(99)00492-9

Reference yield: 75.0%

(6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose (201660-34-6) → (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-galacto-pyranos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-gluco-pyranose + (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-galacto-pyranos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose (201660-35-7)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 0.5h;

DOI:10.1016/S0957-4166(99)00492-9

Reference yield:

(6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose (201660-34-6) → (1R,2R,6R,7R,8R,9R)-8-Benzyloxy-4,4-dimethyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-3,5,10,12-tetraoxa-tricyclo[7.2.1.02,7]dodecane

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / NaBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

2: 50 percent / Drierite; pTsOH / acetone / 4 h / 20 °C

With calcium sulfate; sodium tetrahydroborate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetone; 1: Reduction / 2: ketalization;

DOI:10.1016/S0957-4166(99)00492-9

upstream raw materials:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose

Downstream raw materials:

(6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-galacto-pyranos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose