(2S,4R,5S)-(4-hydroxy-5-methyltetrahydrofuran-2-yl)methanol

Base Information

• Chemical Name: (2S,4R,5S)-(4-hydroxy-5-methyltetrahydrofuran-2-yl)methanol
• CAS No.: 75499-86-4
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.159
• Mol file: 75499-86-4.mol

Synonyms:(2S,4R,5S)-(4-hydroxy-5-methyltetrahydrofuran-2-yl)methanol

Chemical Property of (2S,4R,5S)-(4-hydroxy-5-methyltetrahydrofuran-2-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,5S)-(4-hydroxy-5-methyltetrahydrofuran-2-yl)methanol

There total 6 articles about (2S,4R,5S)-(4-hydroxy-5-methyltetrahydrofuran-2-yl)methanol 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (2S,4R,5S)-(4-hydroxy-5-methyltetrahydrofuran-2-yl)methanol (75499-86-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

2.1: 95 percent / DIBAL / CH₂Cl₂ / 2 h / -78 °C

3.1: 77 percent / mesyl chloride; triethylamine / CH₂Cl₂ / 2.5 h / -20 - 40 °C

4.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 - 0 °C

4.2: 85 percent / TMEDA / tetrahydrofuran / 12 h / 20 °C

5.1: ThxBH₂ / tetrahydrofuran / 16 h / 0 °C

5.2: 59 percent / aq. NaOH; aq. H₂O₂ / 6 h / 20 °C

6.1: 93 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

With dmap; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2007.03.014

Reference yield:

(S)-2-(2-Benzyloxy-ethoxy)-propionic acid (124251-97-4) → (2S,3S,5R)-5-Hydroxymethyl-2-methyl-tetrahydro-furan-3-ol (75499-86-4,82109-99-7,110173-10-9,124375-79-7)

Guidance literature:

Multi-step reaction with 4 steps

1: (COCl)2, cat. DMF

3: 47 percent / 1 weight percent rhodium acetate / CH₂Cl₂

4: 1) H₂; 2) NaHB(OAc)3, 4A molecular sieves / 1) Pd(OH)2;

With oxalyl dichloride; 4 A molecular sieve; hydrogen; sodium tris(acetoxy)borohydride; N,N-dimethyl-formamide; rhodium(II) acetate; palladium dihydroxide; In dichloromethane;

DOI:10.1016/S0040-4039(00)99571-6

Reference yield:

(S)-2-(2-Benzyloxy-ethoxy)-propionyl chloride → (2S,3S,5R)-5-Hydroxymethyl-2-methyl-tetrahydro-furan-3-ol (75499-86-4,82109-99-7,110173-10-9,124375-79-7)

Guidance literature:

Multi-step reaction with 3 steps

2: 47 percent / 1 weight percent rhodium acetate / CH₂Cl₂

3: 1) H₂; 2) NaHB(OAc)3, 4A molecular sieves / 1) Pd(OH)2;

With 4 A molecular sieve; hydrogen; sodium tris(acetoxy)borohydride; rhodium(II) acetate; palladium dihydroxide; In dichloromethane;

DOI:10.1016/S0040-4039(00)99571-6

upstream raw materials:

(S)-5-Benzyloxymethyl-2-methyl-dihydro-furan-3-one

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

(S)-2-(2-Benzyloxy-ethoxy)-propionic acid

(S)-3-(2-Benzyloxy-ethoxy)-1-diazo-butan-2-one

Downstream raw materials:

2,5-anhydro-1,4-dideoxy-6-O-(p-tolylsulphonyl)-D-ribo-hexitol

(+)-muscarine iodide

(+)-muscarine toluene-p-sulfonate salt

(+)-muscarine chloride