1-O-benzyl-2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose

Base Information

• Chemical Name: 1-O-benzyl-2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose
• CAS No.: 159299-73-7
• Molecular Formula: C₂₁H₃₀O₆
• Molecular Weight: 378.466
• Mol file: 159299-73-7.mol

Synonyms:1-O-benzyl-2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose

Chemical Property of 1-O-benzyl-2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-benzyl-2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose

There total 5 articles about 1-O-benzyl-2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose 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:

2,3:4,6-bis-O-isopropylidene-L-sorbose (17682-70-1) → 1-O-benzyl-2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose (159299-73-7)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridinium chlorochromate, 4A sieves / CH₂Cl₂ / 12 h / Ambient temperature

2: CH₂Cl₂ / 24 h / Ambient temperature

3: 83 percent / H₂ / 10percent Pd/C / methanol / 4 h / 3040 Torr

4: 85 percent / LiAlH₄ / tetrahydrofuran / 7 h / Heating

5: t-BuOK / 1.) THF, RT, 0.5 h, 2.) THF, RT, 1 h

With lithium aluminium tetrahydride; 4 A molecular sieve; potassium tert-butylate; hydrogen; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0008-6215(94)84020-2

Reference yield:

(3aS,3bR,7aS,8aR)-2,2,5,5-tetramethyltetrahydro-8aH-[1,3]dioxolo[4′,5′:4,5]furo[3,2-d][1,3]dioxine-8a-carbaldehyde (55385-72-3) → 1-O-benzyl-2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose (159299-73-7)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 24 h / Ambient temperature

2: 83 percent / H₂ / 10percent Pd/C / methanol / 4 h / 3040 Torr

3: 85 percent / LiAlH₄ / tetrahydrofuran / 7 h / Heating

4: t-BuOK / 1.) THF, RT, 0.5 h, 2.) THF, RT, 1 h

With lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0008-6215(94)84020-2

Reference yield:

(E)-3-((3aS,3bR,7aS,8aS)-2,2,5,5-Tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-8a-yl)-acrylic acid methyl ester (159299-69-1) → 1-O-benzyl-2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose (159299-73-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / H₂ / 10percent Pd/C / methanol / 4 h / 3040 Torr

2: 85 percent / LiAlH₄ / tetrahydrofuran / 7 h / Heating

3: t-BuOK / 1.) THF, RT, 0.5 h, 2.) THF, RT, 1 h

With lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/0008-6215(94)84020-2

upstream raw materials:

benzyl bromide

2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranose

methyl 2,3-dideoxy-4,5:6,8-di-O-isopropylidene-α-L-xylo-oct-4-ulofuranosonate

2,3:4,6-bis-O-isopropylidene-L-sorbose

Downstream raw materials:

1-O-benzyl-2,3-dideoxy-4,5-O-isopropylidene-α-L-xylo-oct-4-ulofuranose

1-O-benzyl-2,3,6,8,9-pentadeoxy-4,5-O-isopropylidene-α-L-erythro-non-4-ulofuranose

1-O-benzyl-2,3,6-trideoxy-4,5-O-isopropylidene-α-L-erythro-oct-4-ulofuranose

1-O-benzyl-2,3,6-trideoxy-4,5-O-isopropylidene-8-O-(p-toluenesulfonyl)-α-L-erythro-oct-4-ulofuranose