Benzyl 2,3,6-Trideoxy-3-C-formyl-6-C-propyl-D-galactofuranoside γ-Lactone

Base Information

• Chemical Name: Benzyl 2,3,6-Trideoxy-3-C-formyl-6-C-propyl-D-galactofuranoside γ-Lactone
• CAS No.: 147437-40-9
• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.375
• Mol file: 147437-40-9.mol

Synonyms:Benzyl 2,3,6-Trideoxy-3-C-formyl-6-C-propyl-D-galactofuranoside γ-Lactone

Chemical Property of Benzyl 2,3,6-Trideoxy-3-C-formyl-6-C-propyl-D-galactofuranoside γ-Lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 2,3,6-Trideoxy-3-C-formyl-6-C-propyl-D-galactofuranoside γ-Lactone

There total 21 articles about Benzyl 2,3,6-Trideoxy-3-C-formyl-6-C-propyl-D-galactofuranoside γ-Lactone 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: 87.0%

Benzyl 2,3,6-Trideoxy-3-C-carboxyl-6-C-propyl-D-galactofuranoside γ-Lactone (147437-39-6) → Benzyl 2,3,6-Trideoxy-3-C-formyl-6-C-propyl-D-galactofuranoside γ-Lactone (147437-40-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)97761-X

Reference yield:

furan-3-methanol (4412-91-3) → Benzyl 2,3,6-Trideoxy-3-C-formyl-6-C-propyl-D-galactofuranoside γ-Lactone (147437-40-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) BuLi / 1a) hexane, -78 deg C, 4 h, 1b) 0 deg C, 2 h, 2a) THF, -78 deg C, 20 min, 2b) r.t., 40 min

2: imidazole / dimethylformamide / 1 h / Ambient temperature

3: 77 percent / m-chloroperbenzoic acid, NaOAc / CHCl₃ / 1 h / Ambient temperature

4: 67 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2.5 h / Ambient temperature

5: 96 percent / H₂ / 10percent Pd-C / ethyl acetate / 1 h / 760 Torr / Ambient temperature

6: 81 percent / L-selectride / tetrahydrofuran / 1 h / -78 °C

7: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 10 h / Ambient temperature

8: 92 percent / nBu₄NF / tetrahydrofuran / 1 h / Ambient temperature

9: 1) oxalyl chloride, DMSO / 1) CH₂Cl₂, -78 deg C, 10 min, 2) CH₂Cl₂, -78 deg C, 20 min

10: 88 percent / NaClO₂, KH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.5 h / Ambient temperature

11: 93 percent / 2percent HCl / tetrahydrofuran / 2.5 h / Ambient temperature

12: 79 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

13: 87 percent / iBu₂AlH / tetrahydrofuran; toluene / 0.5 h / -78 °C

With 1H-imidazole; hydrogenchloride; sodium chlorite; potassium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)85812-9

Reference yield:

1-<2-(3-Hydroxymethylfuryl)>-1-pentanol (131719-82-9) → Benzyl 2,3,6-Trideoxy-3-C-formyl-6-C-propyl-D-galactofuranoside γ-Lactone (147437-40-9)

Guidance literature:

Multi-step reaction with 12 steps

1: imidazole / dimethylformamide / 1 h / Ambient temperature

2: 77 percent / m-chloroperbenzoic acid, NaOAc / CHCl₃ / 1 h / Ambient temperature

3: 67 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2.5 h / Ambient temperature

4: 96 percent / H₂ / 10percent Pd-C / ethyl acetate / 1 h / 760 Torr / Ambient temperature

5: 81 percent / L-selectride / tetrahydrofuran / 1 h / -78 °C

6: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 10 h / Ambient temperature

7: 92 percent / nBu₄NF / tetrahydrofuran / 1 h / Ambient temperature

8: 1) oxalyl chloride, DMSO / 1) CH₂Cl₂, -78 deg C, 10 min, 2) CH₂Cl₂, -78 deg C, 20 min

9: 88 percent / NaClO₂, KH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.5 h / Ambient temperature

10: 93 percent / 2percent HCl / tetrahydrofuran / 2.5 h / Ambient temperature

11: 79 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

12: 87 percent / iBu₂AlH / tetrahydrofuran; toluene / 0.5 h / -78 °C

With 1H-imidazole; hydrogenchloride; sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)85812-9

upstream raw materials:

Benzyl 2,3,6-Trideoxy-3-C-carboxyl-6-C-propyl-D-galactofuranoside γ-Lactone

furan-3-methanol

pentanal

1-<2-(3-Hydroxymethylfuryl)>-1-pentanol

Downstream raw materials:

(3aS,6R,6aR)-2-Benzyloxy-6-butyl-4-(1-ethoxy-ethoxy)-hexahydro-furo[3,4-b]furan