(2R,3S,4R)-2-((R)-Hydroxy-phenyl-methyl)-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2R,3S,4R)-2-((R)-Hydroxy-phenyl-methyl)-tetrahydro-pyran-3,4-diol
• CAS No.: 282094-39-7
• Molecular Formula: C₁₂H₁₆O₄
• Molecular Weight: 224.257
• Mol file: 282094-39-7.mol

Synonyms:(2R,3S,4R)-2-((R)-Hydroxy-phenyl-methyl)-tetrahydro-pyran-3,4-diol

Chemical Property of (2R,3S,4R)-2-((R)-Hydroxy-phenyl-methyl)-tetrahydro-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-2-((R)-Hydroxy-phenyl-methyl)-tetrahydro-pyran-3,4-diol

There total 8 articles about (2R,3S,4R)-2-((R)-Hydroxy-phenyl-methyl)-tetrahydro-pyran-3,4-diol 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%

(R)-((2R,3S,4R)-3,4-Bis-methoxymethoxy-tetrahydro-pyran-2-yl)-phenyl-methanol (282094-27-3) → (2R,3S,4R)-2-((R)-Hydroxy-phenyl-methyl)-tetrahydro-pyran-3,4-diol (282094-39-7)

Guidance literature:

With dimethylaluminum chloride; In dichloromethane;

DOI:10.1016/S0040-4039(00)00174-X

Reference yield:

D-glucal triacetate (2873-29-2) → (2R,3S,4R)-2-((R)-Hydroxy-phenyl-methyl)-tetrahydro-pyran-3,4-diol (282094-39-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / H₂ / Pd/C / methanol

2.1: 100 percent / NaOMe / methanol

3.1: 70 percent / Et₃N / dimethylformamide

4.1: 75 percent / iPr₂NEt / CH₂Cl₂

5.1: 88 percent / TBAF / tetrahydrofuran

6.1: PDC / dimethylformamide; H₂O

6.2: EDCl; MeNHOMe; DMAP / CH₂Cl₂; triethylamine

6.3: tetrahydrofuran

7.1: 87 percent / NaBH₄ / methanol

8.1: 99 percent / Me₂AlCl / CH₂Cl₂

With sodium tetrahydroborate; dipyridinium dichromate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; dimethylaluminum chloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Catalytic hydrogenation / 2.1: Deacetylation / 3.1: silylation / 4.1: Substitution / 5.1: desilylation / 6.1: Oxidation / 6.2: Substitution / 6.3: Grignard reaction / 7.1: Reduction / 8.1: Elimination;

DOI:10.1016/S0040-4039(00)00174-X

Reference yield:

(3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran (3971-47-9,7103-29-9,13035-11-5,26242-03-5) → (2R,3S,4R)-2-((R)-Hydroxy-phenyl-methyl)-tetrahydro-pyran-3,4-diol (282094-39-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 70 percent / Et₃N / dimethylformamide

2.1: 75 percent / iPr₂NEt / CH₂Cl₂

3.1: 88 percent / TBAF / tetrahydrofuran

4.1: PDC / dimethylformamide; H₂O

4.2: EDCl; MeNHOMe; DMAP / CH₂Cl₂; triethylamine

4.3: tetrahydrofuran

5.1: 87 percent / NaBH₄ / methanol

6.1: 99 percent / Me₂AlCl / CH₂Cl₂

With sodium tetrahydroborate; dipyridinium dichromate; tetrabutyl ammonium fluoride; dimethylaluminum chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Substitution / 3.1: desilylation / 4.1: Oxidation / 4.2: Substitution / 4.3: Grignard reaction / 5.1: Reduction / 6.1: Elimination;

DOI:10.1016/S0040-4039(00)00174-X

upstream raw materials:

(R)-((2R,3S,4R)-3,4-Bis-methoxymethoxy-tetrahydro-pyran-2-yl)-phenyl-methanol

(3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran

(2R,3S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diol

((2R,3S,4R)-3,4-Bis-methoxymethoxy-tetrahydro-pyran-2-yl)-methanol