(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethanol

Base Information

• Chemical Name: (R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethanol
• CAS No.: 16354-89-5
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• DSSTox Substance ID: DTXSID401210484
• Nikkaji Number: J1.282.579J
• Mol file: 16354-89-5.mol

Synonyms:16354-89-5;DTXSID401210484;(alphaR,4R)-2,2-Dimethyl-alpha-phenyl-1,3-dioxolane-4-methanol;(R)-alpha-(2,2-Dimethyl-1,3-dioxolane-4beta-yl)benzyl alcohol

Chemical Property of (R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethanol

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 209

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OCC(O1)C(C2=CC=CC=C2)O)C
• Isomeric SMILES: CC1(OC[C@@H](O1)[C@@H](C2=CC=CC=C2)O)C

Technology Process of (R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethanol

There total 11 articles about (R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethanol 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: 85.0%

phenylmagnesium bromide (100-58-3) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol (16354-89-5)

Guidance literature:

phenylmagnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

2,3-isopropylidene-glyceraldehyde; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c02884

Reference yield: 66.0%

phenylmagnesium chloride (100-59-4) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol (16354-89-5) + (S)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol (16354-91-9)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2h;

Reference yield:

1,2:5,6-di-O-isopropylidene-D-mannitol (64870-23-1) → (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol (16354-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium periodate / water; dichloromethane / 0.67 h

2.1: copper(l) iodide / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

With sodium periodate; copper(l) iodide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/acs.orglett.0c02884

upstream raw materials:

phenylmagnesium bromide

2,3-isopropylidene-glyceraldehyde

phenyllithium

[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenylmethanone

Downstream raw materials:

(R)-4-((R)-Benzyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolane

(R)-4-((S)-Benzyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolane

(1R,2R)-1-phenylpropane-1,2,3-triol

(R)-4-((R)-Allyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolane