(5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one

Base Information

• Chemical Name: (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one
• CAS No.: 127940-37-8
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.218
• Mol file: 127940-37-8.mol

Synonyms:(5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one

Chemical Property of (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one

There total 2 articles about (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one 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: 86.0%

(furan-2-yloxy)-trimethylsilane (61550-02-5) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one (127940-37-8) + (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one (127940-36-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -80 ℃; for 6h;

DOI:10.1016/S0040-4020(01)87777-2

Reference yield: 13.0%

(furan-2-yloxy)-trimethylsilane (61550-02-5) + (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (22323-80-4) → (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one (127940-37-8) + (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one (127940-36-7)

Guidance literature:

With boron trifluoride diethyl etherate; sodium hydrogencarbonate; In dichloromethane; at -78 ℃; for 6h;

DOI:10.1016/S0040-4039(01)93777-3

Reference yield:

(5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one (127940-37-8) → (1S,2S,3S,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol (105265-95-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / NaBH₄; NiCl₂*6H₂O / methanol / 2 h / 0 °C

2: 91 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

3: 90 percent / aq. acetic acid / 50 °C

4: 88 percent / aq. NaIO₄; SiO₂ / CH₂Cl₂ / 20 °C

5: 41 percent / diisopropylethylamine / CH₂Cl₂ / 4 h / 20 °C

6: 70 percent / LiBH₄ / tetrahydrofuran / 0.5 h / 0 °C

7: 100 percent / aq. HCl / tetrahydrofuran; methanol / 2 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; lithium borohydride; silica gel; acetic acid; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo010585v

upstream raw materials:

(furan-2-yloxy)-trimethylsilane

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(1S,2S,3S,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol

4a-carba-β-L-lyxofuranose