(S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-butan-1-ol

Base Information

• Chemical Name: (S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-butan-1-ol
• CAS No.: 180889-64-9
• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.39
• Mol file: 180889-64-9.mol

Synonyms:(S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-butan-1-ol

Chemical Property of (S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-butan-1-ol

There total 2 articles about (S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-butan-1-ol 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:

2,3-isopropylidene-glyceraldehyde (15186-48-8) + (3-((4-methoxybenzyl)oxy)propyl)magnesium bromide → (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol (181137-83-7) + (S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-butan-1-ol (180889-64-9)

Guidance literature:

With copper(l) iodide; 2,3-dimercapto-succinic acid; In tetrahydrofuran; at -78 - 20 ℃; Yield given; Yields of byproduct given;

Reference yield:

1-[(3-bromopropoxy)methyl]-4-methoxybenzene (147193-45-1) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol (181137-83-7) + (S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-butan-1-ol (180889-64-9)

Guidance literature:

With magnesium; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF; 2.) THF, -78 deg C to r.t.;

DOI:10.1016/0040-4039(96)01136-7

Reference yield:

(S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-butan-1-ol (180889-64-9) → (2S,3S,5S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-5-vinyl-tetrahydro-furan-3-ol (180889-66-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaH; 2.) Bu₄NI / 1.) DMF, r.t.; 2.) DMF, r.t.

2: CF₃CO₂H / tetrahydrofuran; H₂O / Heating

3: NaIO₄ / tetrahydrofuran; H₂O / Ambient temperature

4: PDC / dimethylformamide / Ambient temperature

5: Et₃N / diethyl ether / Ambient temperature

6: diethyl ether / 0 deg C to r.t.

7: Rh₂(O₂CCPh₃)4 / CH₂Cl₂ / Ambient temperature

8: CH₂Cl₂ / -78 - -10 °C

With sodium periodate; dipyridinium dichromate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; trifluoroacetic acid; dirhodium(II) tetrakis(triphenylacetate); In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)01136-7

upstream raw materials:

1-[(3-bromopropoxy)methyl]-4-methoxybenzene

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(R)-4-[(S)-1-Allyloxy-4-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxolane

(S)-2-Allyloxy-5-(4-methoxy-benzyloxy)-pentanal

(2S,3S,5S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-5-vinyl-tetrahydro-furan-3-ol

(S)-2-Allyloxy-5-(4-methoxy-benzyloxy)-pentanoic acid