3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-propionic acid

Base Information

• Chemical Name: 3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-propionic acid
• CAS No.: 204906-08-1
• Molecular Formula: C₁₃H₁₆O₅
• Molecular Weight: 252.267
• Mol file: 204906-08-1.mol

Synonyms:

Chemical Property of 3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-propionic acid

There total 10 articles about 3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-propionic acid 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:

(1R)-1-((4R,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol (168109-89-5) → 3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-propionic acid (204906-08-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / aq. sodium periodate

2: tetrahydrofuran

3: 90 percent / HCl; EtOH / Acid hydrolysis

4: 70 percent / copper(II) chloride; sodium acetate / palladium(II) chloride / acetic acid / 20 °C

5: 90 percent / diisobutylaluminum hydride / CH₂Cl₂ / -78 °C

6: 55 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran

7: sulfuric acid / dioxane

8: Ag₂O; aq. NaOH

With hydrogenchloride; sodium hydroxide; sodium periodate; ethanol; sulfuric acid; potassium tert-butylate; sodium acetate; diisobutylaluminium hydride; copper dichloride; silver(l) oxide; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid; tert-butyl alcohol; 2: Grignard reaction / 6: Wittig reaction;

DOI:10.1016/S0040-4039(02)01599-X

Reference yield:

mannitol (69-65-8) → 3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-propionic acid (204906-08-1)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂SO₄

2: 90 percent / aq. sodium periodate

3: tetrahydrofuran

4: 90 percent / HCl; EtOH / Acid hydrolysis

5: 70 percent / copper(II) chloride; sodium acetate / palladium(II) chloride / acetic acid / 20 °C

6: 90 percent / diisobutylaluminum hydride / CH₂Cl₂ / -78 °C

7: 55 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran

8: sulfuric acid / dioxane

9: Ag₂O; aq. NaOH

With hydrogenchloride; sodium hydroxide; sodium periodate; ethanol; sulfuric acid; potassium tert-butylate; sodium acetate; diisobutylaluminium hydride; copper dichloride; silver(l) oxide; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid; tert-butyl alcohol; 4: Grignard reaction / 8: Wittig reaction;

DOI:10.1016/S0040-4039(02)01599-X

Reference yield:

mannitol triacetonide (3969-59-3) → 3-((2S,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-propionic acid (204906-08-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / aq. sodium periodate

2: tetrahydrofuran

3: 90 percent / HCl; EtOH / Acid hydrolysis

4: 70 percent / copper(II) chloride; sodium acetate / palladium(II) chloride / acetic acid / 20 °C

5: 90 percent / diisobutylaluminum hydride / CH₂Cl₂ / -78 °C

6: 55 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran

7: sulfuric acid / dioxane

8: Ag₂O; aq. NaOH

With hydrogenchloride; sodium hydroxide; sodium periodate; ethanol; sulfuric acid; potassium tert-butylate; sodium acetate; diisobutylaluminium hydride; copper dichloride; silver(l) oxide; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid; tert-butyl alcohol; 3: Grignard reaction / 7: Wittig reaction;

DOI:10.1016/S0040-4039(02)01599-X

upstream raw materials:

(1R)-1-((4R,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol

mannitol

mannitol triacetonide

(1R,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol

Downstream raw materials:

methyl 3-([2S,3S,4R,5R]-3,4-dihydroxy-5-phenyltetrahydrofuran-2-yl)propionate