Phenyl 2,3-di-O-allyl-4-[2-(2-chloroethoxy)ethyl]-6-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 2,3-di-O-allyl-4-[2-(2-chloroethoxy)ethyl]-6-O-benzyl-β-D-glucopyranoside
• CAS No.: 342813-52-9
• Molecular Formula: C₂₉H₃₇ClO₇
• Molecular Weight: 533.062

Synonyms:Phenyl 2,3-di-O-allyl-4-[2-(2-chloroethoxy)ethyl]-6-O-benzyl-β-D-glucopyranoside

Chemical Property of Phenyl 2,3-di-O-allyl-4-[2-(2-chloroethoxy)ethyl]-6-O-benzyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of Phenyl 2,3-di-O-allyl-4-[2-(2-chloroethoxy)ethyl]-6-O-benzyl-β-D-glucopyranoside

There total 2 articles about Phenyl 2,3-di-O-allyl-4-[2-(2-chloroethoxy)ethyl]-6-O-benzyl-β-D-glucopyranoside 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: 84.0%

3-oxa-1,5-dichloropentane (111-44-4) + Phenyl 2,3-di-O-allyl-6-O-benzyl-β-D-glucopyranoside (342813-51-8) → Phenyl 2,3-di-O-allyl-4-[2-(2-chloroethoxy)ethyl]-6-O-benzyl-β-D-glucopyranoside (342813-52-9)

Guidance literature:

With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; at 50 ℃; for 5h;

DOI:10.1055/s-2001-12357

Reference yield:

Phenyl 2,3-di-O-allyl-4,6-O-benzylidene-β-D-glucopyranoside → Phenyl 2,3-di-O-allyl-4-[2-(2-chloroethoxy)ethyl]-6-O-benzyl-β-D-glucopyranoside (342813-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / NaBH₃CN; HCl; molecular sieve 3 Angstroem / tetrahydrofuran; diethyl ether / 16 h / 20 °C

2: 84 percent / aq. KOH; [Bu₄N]HSO₄ / tetrahydrofuran / 5 h / 50 °C

With hydrogenchloride; potassium hydroxide; 3 A molecular sieve; tetra(n-butyl)ammonium hydrogensulfate; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether;

DOI:10.1055/s-2001-12357

Reference yield: 72.0%

Phenyl 2,3-di-O-allyl-4-[2-(2-chloroethoxy)ethyl]-6-O-benzyl-β-D-glucopyranoside (342813-52-9) + diethylene glycol (111-46-6) → Phenyl 2,3-di-O-allyl-6-O-benzyl-4-O-{2-[ω-hydroxytri(oxyethylene)ethyl]}-β-D-glucopyranoside (342813-53-0)

Guidance literature:

With potassium hydroxide; at 80 - 90 ℃; for 5h;

DOI:10.1055/s-2001-12357

upstream raw materials:

3-oxa-1,5-dichloropentane

Phenyl 2,3-di-O-allyl-6-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

Phenyl 2,3-di-O-allyl-6-O-benzyl-4-O-{2-[ω-hydroxytri(oxyethylene)ethyl]}-β-D-glucopyranoside

Phenyl 2,3-di-O-allyl-6-O-benzyl-4-O-{2-[ω-hydroxytetra(oxyethylene)ethyl]}-β-D-glucopyranoside

6-O-Benzyl-1,4-O-(3,6,9-trioxaundecan-1,11-diyl)-α-D-glucopyranose

6-O-Benzyl-1,4-O-(3,6,9,12-tetraoxatetradecan-1,14-diyl)-α-D-glucopyranose

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