(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde

Base Information

Chemical Name:(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde
CAS No.:179944-88-8
Molecular Formula:C₁₇H₂₄O₄
Molecular Weight:292.375
Hs Code.:

Synonyms:(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde

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Chemical Property of (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde

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Technology Process of (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde

There total 23 articles about (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde 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: 99.0%

: 740836-23-1
(2R,3R)-2-((E)-(1S,2R)-2-Benzyloxy-1-methyl-pent-3-enyl)-5-methoxy-3-methyl-tetrahydro-furan

: 179944-88-8
(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde

Guidance literature:: (2R,3R)-2-((E)-(1S,2R)-2-Benzyloxy-1-methyl-pent-3-enyl)-5-methoxy-3-methyl-tetrahydro-furan; With osmium(VIII) oxide; N-methyl-2-indolinone; water; In acetone; at 20 ℃;

With sodium periodate; at 20 ℃; Further stages.;
DOI:10.1016/j.tetlet.2004.05.078

Reference yield: 97.0%

: 157220-49-0
(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol

: 179944-88-8
(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃;
DOI:10.1016/0040-4039(94)88035-2

Reference yield:

: 162255-08-5
(2S,3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylbutanamide

: 179944-88-8
(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde

Guidance literature:: Multi-step reaction with 13 steps

1: 100 percent / imidazole / dimethylformamide / 5.5 h / 23 °C

2: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

3: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

4: 97 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

5: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1.5 h / -23 °C

6: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 4 deg C

7: 100 percent / pyridine / 5 h / 0 °C

8: 91 percent / dimethylsulfoxide / 2.5 h / 50 °C

10: 100 percent / sodium, liquid ammonia / tetrahydrofuran / 0.5 h / -78 °C

11: 100 percent / imidazole / dimethylformamide / 1.3 h / 0 °C

12: 1.) NaH, 2.) Bu₄NF / 1.) DMF, mineral oil, 0 -> 23 deg C, 2.) THF, 23 deg C, 13 h

13: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 18 h, 2.) CH₂Cl₂, 0 deg C, 25 min

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; oxalyl dichloride; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9606113