(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carbaldehyde

Base Information

Chemical Name:(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carbaldehyde
CAS No.:87599-03-9
Molecular Formula:C₁₇H₂₄O₃
Molecular Weight:276.376
Hs Code.:

Synonyms:(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carbaldehyde

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Chemical Property of (2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carbaldehyde

Chemical Property:

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Technology Process of (2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carbaldehyde

There total 16 articles about (2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carbaldehyde 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:

: 87678-22-6
benzyl 2(R)-<5(R)-(hydroxymethyl)-3(R)-methyl-2(R)-tetrahydrofuryl>butyl ether

: 87599-03-9
(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃; for 2h;
DOI:10.1021/jo00174a008

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
L-(+)-arabinose

: 87599-03-9
(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 15 steps

1: 82 percent / acetyl chloride / 1.) 0 deg C, 2.) 50 deg C, 24 h

2: 99.8 percent / p-toluenesulfonic acid / acetone / 36 h / Ambient temperature

3: 93 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 2 h / -60 °C

4: 80 percent / diethyl ether / 1.) -78 deg C, 45 min, 2.) room temp., 1 h

5: 78 percent / 4percent aq. H₂SO₄ / methanol / 22 h / Heating

6: 90 percent / deionized water, bromine, calcium carbonate, / 0.5 h / Ambient temperature

7: 99 percent / P₂O₅/Celite / CHCl₃ / 1.) 0 deg C, 2.) room temp., 1 h

8: 99.7 percent / 1M diisobutylaluminum hydride / diethyl ether; hexane / 1 h / -78 °C

9: 79 percent / 1.) tris(dimethylamino)phosphine, 2.) lithium wire, anhydrous ammonia / tetrahydrofuran / 1.) -78 deg C, 30 min, then to room temp., 2.) -78 deg C, 2 h

11: 75 percent / H₂ / 5percent Pt/C / ethyl acetate / 12 h / 760 Torr

12: 95 percent / lithium tetrahydridoaluminate / diethyl ether / 1 h / 0 °C

13: 99 percent / potassium hydride / tetrahydrofuran / 1 h / Ambient temperature

14: aq. 10percent HCl / tetrahydrofuran / 12 h / 50 °C

15: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 2 h / -60 °C

With hydrogenchloride; lithium aluminium tetrahydride; oxalyl dichloride; Celite; sulfuric acid; ammonia; water; hydrogen; bromine; phosphorus pentoxide; lithium; potassium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; acetyl chloride; calcium carbonate; Hexamethylphosphorous triamide; platinum on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; ethyl acetate; acetone;
DOI:10.1021/jo00174a008

Reference yield:

: 65247-32-7
benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside

: 87599-03-9
(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 12 steps

1: 80 percent / diethyl ether / 1.) -78 deg C, 45 min, 2.) room temp., 1 h

2: 78 percent / 4percent aq. H₂SO₄ / methanol / 22 h / Heating

3: 90 percent / deionized water, bromine, calcium carbonate, / 0.5 h / Ambient temperature

4: 99 percent / P₂O₅/Celite / CHCl₃ / 1.) 0 deg C, 2.) room temp., 1 h

5: 99.7 percent / 1M diisobutylaluminum hydride / diethyl ether; hexane / 1 h / -78 °C

6: 79 percent / 1.) tris(dimethylamino)phosphine, 2.) lithium wire, anhydrous ammonia / tetrahydrofuran / 1.) -78 deg C, 30 min, then to room temp., 2.) -78 deg C, 2 h

8: 75 percent / H₂ / 5percent Pt/C / ethyl acetate / 12 h / 760 Torr

9: 95 percent / lithium tetrahydridoaluminate / diethyl ether / 1 h / 0 °C

10: 99 percent / potassium hydride / tetrahydrofuran / 1 h / Ambient temperature

11: aq. 10percent HCl / tetrahydrofuran / 12 h / 50 °C

12: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 2 h / -60 °C

With hydrogenchloride; lithium aluminium tetrahydride; oxalyl dichloride; Celite; sulfuric acid; ammonia; water; hydrogen; bromine; phosphorus pentoxide; lithium; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; calcium carbonate; Hexamethylphosphorous triamide; platinum on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; ethyl acetate;
DOI:10.1021/jo00174a008