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

Base Information

• Chemical Name: 1-O-benzyl-2,3,6-trideoxy-4,5-O-isopropylidene-α-L-erythro-oct-4-ulofuranose
• CAS No.: 159299-78-2
• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.401
• Mol file: 159299-78-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 1-O-benzyl-2,3,6-trideoxy-4,5-O-isopropylidene-α-L-erythro-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: 56.0%

1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3,6-trideoxy-4,5-O-isopropylidene-α-L-erythro-oct-4-ulofuranose (159299-77-1) → 1-O-benzyl-2,3,6-trideoxy-4,5-O-isopropylidene-α-L-erythro-oct-4-ulofuranose (159299-78-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In toluene; Ambient temperature;

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

Reference yield:

2,3:4,6-bis-O-isopropylidene-L-sorbose (17682-70-1) → 1-O-benzyl-2,3,6-trideoxy-4,5-O-isopropylidene-α-L-erythro-oct-4-ulofuranose (159299-78-2)

Guidance literature:

Multi-step reaction with 10 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

6: 100 percent / 50percent AcOH / 1 h / 50 °C

7: 100 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

8: 90 percent / NaH, imidazole / tetrahydrofuran / 1.25 h / Ambient temperature

9: 86 percent / Bu₃SnH, AIBN / toluene / Heating

10: 56 percent / TBAF*3H₂O / toluene / Ambient temperature

With 1H-imidazole; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hydride; acetic acid; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene;

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-2,3,6-trideoxy-4,5-O-isopropylidene-α-L-erythro-oct-4-ulofuranose (159299-78-2)

Guidance literature:

Multi-step reaction with 9 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

5: 100 percent / 50percent AcOH / 1 h / 50 °C

6: 100 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

7: 90 percent / NaH, imidazole / tetrahydrofuran / 1.25 h / Ambient temperature

8: 86 percent / Bu₃SnH, AIBN / toluene / Heating

9: 56 percent / TBAF*3H₂O / toluene / Ambient temperature

With 1H-imidazole; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hydride; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene;

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

upstream raw materials:

1-O-benzyl-8-O-tert-butyldiphenylsilyl-2,3,6-trideoxy-4,5-O-isopropylidene-α-L-erythro-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

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

Downstream raw materials:

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

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