(2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol

Base Information

• Chemical Name: (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol
• CAS No.: 181137-83-7
• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.39
• Mol file: 181137-83-7.mol

Synonyms:(2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol

Chemical Property of (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol

There total 3 articles about (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol 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: 93.0%

1-[(3-bromopropoxy)methyl]-4-methoxybenzene (147193-45-1) + 1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0) → (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol (181137-83-7)

Guidance literature:

1-[(3-bromopropoxy)methyl]-4-methoxybenzene; With magnesium; ethylene dibromide; In tetrahydrofuran; at 20 ℃; for 2h;

1,2-O-isopropylidene-D-glycerol; With copper(l) iodide; dimethylsulfide; In tetrahydrofuran; at 20 ℃; for 15h; Further stages.;

DOI:10.1021/jo702111u

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

upstream raw materials:

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

2,3-isopropylidene-glyceraldehyde

1,2-O-isopropylidene-D-glycerol

Downstream raw materials:

(2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]-3-{(3S)-3-methyl-2-methylene-4-[(triisopropylsilyl)oxy]butoxy}hexane-1,2-diol

4-O-(cyclohex-1-en-1-ylmethyl)-2,3-dideoxy-1-O-(4-methoxybenzyl)-5,6-O-(1-methylidene)-D-threo-hexitol

(2R)-5-[(4-methoxybenzyl)oxy]-2-{(3S)-3-methyl-2-methylene-4-[(triisopropylsilyl)oxy]butoxy}pentanal

(3R)-1-diazo-6-[(4-methoxybenzyl)oxy]-2-{(3S)-3-methyl-2-methylene-4-[(triisopropylsilyl)oxy]butoxy}hexan-2-one