(-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol

Base Information

• Chemical Name: (-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol
• CAS No.: 1253890-79-7
• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.202
• Mol file: 1253890-79-7.mol

Synonyms:(-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol

Chemical Property of (-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol

There total 11 articles about (-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-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: 98.0%

(2S,3R,4R)-2-(3,4-bis(benzyloxy)phenyl)tetrahydrofuran-3,4-diol → (-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol (1253890-79-7)

Guidance literature:

With platinum(IV) oxide; hydrogen; In methanol; for 2h; under 1551.49 Torr;

DOI:10.1016/j.tetlet.2016.12.083

Reference yield:

C26H26O5 → (-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol (1253890-79-7)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 4 h / 0 °C

2: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water; toluene / 3 h / 0 °C

3: tin (IV) chloride pentahydrate / dichloromethane / 0.5 h / 0 °C

4: platinum(IV) oxide; hydrogen / methanol / 2 h / 1551.49 Torr

With platinum(IV) oxide; osmium(VIII) oxide; tin (IV) chloride pentahydrate; hydrogen; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 1: |Wittig Olefination;

DOI:10.1016/j.tetlet.2016.12.083

Reference yield:

Methyl caffeate (3843-74-1,67667-67-8) → (-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol (1253890-79-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / acetone / 15 h / 56 °C / Inert atmosphere

2.1: AD-mix-β; methanesulfonamide / tert-butyl alcohol; water / 12 h / 20 °C

3.1: boron trifluoride diethyl etherate / acetone / 2 h

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

5.2: 0.33 h / -78 - 20 °C / Inert atmosphere

6.1: tetrahydrofuran / 4 h / 0 °C

7.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water; toluene / 3 h / 0 °C

8.1: scandium tris(trifluoromethanesulfonate) / dichloromethane / 0.5 h / 0 °C

9.1: hydrogenchloride / water; methanol / 0.5 h / 0 °C

10.1: platinum(IV) oxide; hydrogen / methanol / 2 h / 1551.49 Torr

With hydrogenchloride; platinum(IV) oxide; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; AD-mix-β; hydrogen; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 5.1: |Swern Oxidation / 5.2: |Swern Oxidation / 6.1: |Wittig Olefination;

DOI:10.1016/j.tetlet.2016.12.083

upstream raw materials:

caffeic acid

Methyl caffeate

methyl (E)-3-(3,4-bis(benzyloxy)phenyl)acrylate

((4R,5R)-5-(3,4-bis(benzyloxy)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

Downstream raw materials:

(-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran