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

Base Information

• Chemical Name: 4-O-(cyclohex-1-en-1-ylmethyl)-2,3-dideoxy-1-O-(4-methoxybenzyl)-5,6-O-(1-methylidene)-D-threo-hexitol
• CAS No.: 876058-04-7
• Molecular Formula: C₂₄H₃₆O₅
• Molecular Weight: 404.547
• Mol file: 876058-04-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 4-O-(cyclohex-1-en-1-ylmethyl)-2,3-dideoxy-1-O-(4-methoxybenzyl)-5,6-O-(1-methylidene)-D-threo-hexitol 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: 78.0%

1-bromomethylcyclohexene (37677-17-1) + (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol (181137-83-7) → 4-O-(cyclohex-1-en-1-ylmethyl)-2,3-dideoxy-1-O-(4-methoxybenzyl)-5,6-O-(1-methylidene)-D-threo-hexitol (876058-04-7)

Guidance literature:

(2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol; With sodium hydride; In tetrahydrofuran; for 1h; Heating;

1-bromomethylcyclohexene; In tetrahydrofuran; for 24h; Heating;

DOI:10.1055/s-2005-918485

Reference yield:

4-O-(cyclohex-1-en-1-ylmethyl)-2,3-dideoxy-1-O-(4-methoxybenzyl)-5,6-O-(1-methylidene)-D-threo-hexitol (876058-04-7) → (2R,3R)-3-(Cyclohex-1-enylmethoxy)-6-(4-methoxy-benzyloxy)-hexane-1,2-diol

Guidance literature:

With pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; ethylene glycol; for 20h; Heating;

DOI:10.1055/s-2005-918485

Reference yield:

4-O-(cyclohex-1-en-1-ylmethyl)-2,3-dideoxy-1-O-(4-methoxybenzyl)-5,6-O-(1-methylidene)-D-threo-hexitol (876058-04-7) → (2R)-5-(benzyloxy)-2-(cyclohex-1-en-1-ylmethoxy)pentanal (876058-05-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluene sulfoante / ethane-1,2-diol; tetrahydrofuran; CH₂Cl₂ / 20 h / Heating

2: 4.15 g / aq. sodium periodate / tetrahydrofuran / 1.5 h / 20 °C

With sodium periodate; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; ethylene glycol;

DOI:10.1055/s-2005-918485

upstream raw materials:

1-bromomethylcyclohexene

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

Downstream raw materials:

(2R)-5-(benzyloxy)-2-(cyclohex-1-en-1-ylmethoxy)pentanal

(R)-2-(Cyclohex-1-enylmethoxy)-5-(4-methoxy-benzyloxy)-pentanoic acid

(3R)-3-(cyclohex-1-en-1-ylmethoxy)-1-diazo-6-[(4-methoxybenzyl)oxy]hexan-2-one