acetic acid 3,5-diacetoxy-4-(benzyloxy)-6-ethoxytetrahydropyran-2-ylmethyl ester

Base Information

Chemical Name:acetic acid 3,5-diacetoxy-4-(benzyloxy)-6-ethoxytetrahydropyran-2-ylmethyl ester
CAS No.:289891-10-7
Molecular Formula:C₂₁H₂₈O₉
Molecular Weight:424.448
Hs Code.:

Synonyms:acetic acid 3,5-diacetoxy-4-(benzyloxy)-6-ethoxytetrahydropyran-2-ylmethyl ester

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Chemical Property of acetic acid 3,5-diacetoxy-4-(benzyloxy)-6-ethoxytetrahydropyran-2-ylmethyl ester

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Technology Process of acetic acid 3,5-diacetoxy-4-(benzyloxy)-6-ethoxytetrahydropyran-2-ylmethyl ester

There total 5 articles about acetic acid 3,5-diacetoxy-4-(benzyloxy)-6-ethoxytetrahydropyran-2-ylmethyl ester 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: 35.0%

: 108-24-7
acetic anhydride

: 289891-09-4
acetic acid 5-acetoxy-4-(benzyloxy)-6-ethoxy-5,6-dihydro-4H-pyran-2-ylmethyl ester

: 289891-10-7
acetic acid 3,5-diacetoxy-4-(benzyloxy)-6-ethoxytetrahydropyran-2-ylmethyl ester

Guidance literature:: acetic acid 5-acetoxy-4-(benzyloxy)-6-ethoxy-5,6-dihydro-4H-pyran-2-ylmethyl ester; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃;

In water; at 60 ℃; for 1h;

acetic anhydride; In pyridine; Further stages.;
DOI:10.1021/jo9918596

Reference yield:

: 935-04-6
benzyl vinyl ether

: 289891-10-7
acetic acid 3,5-diacetoxy-4-(benzyloxy)-6-ethoxytetrahydropyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 50 percent / 24 h / 0 °C

2.1: 60 percent / 2,2'-isopropylidenebis[(4S)-4-t-Bu-2-oxazoline]-Cu(OTf)2 / diethyl ether / 16 h / 20 °C

3.1: LiAlH₄ / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.2: 92 percent / pyridine

4.1: BH₃*SMe₂ / tetrahydrofuran / 0 - 20 °C

4.2: 30percent NaOH; 35percent H₂O₂ / H₂O / 1 h / 60 °C

4.3: 35 percent / pyridine

With lithium aluminium tetrahydride; copper(2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline])(triflate)2; dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether; 1.1: Substitution / 2.1: Cycloaddition / 3.1: Reduction / 3.2: Acetylation / 4.1: Reduction / 4.2: Oxidation / 4.3: Acetylation;
DOI:10.1021/jo9918596

Reference yield:

: 129751-10-6
(Z)-1-acetoxy-2-ethoxyethylene

: 289891-10-7
acetic acid 3,5-diacetoxy-4-(benzyloxy)-6-ethoxytetrahydropyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 60 percent / 2,2'-isopropylidenebis[(4S)-4-t-Bu-2-oxazoline]-Cu(OTf)2 / diethyl ether / 16 h / 20 °C

2.1: LiAlH₄ / tetrahydrofuran / 1.5 h / 0 - 20 °C

2.2: 92 percent / pyridine

3.1: BH₃*SMe₂ / tetrahydrofuran / 0 - 20 °C

3.2: 30percent NaOH; 35percent H₂O₂ / H₂O / 1 h / 60 °C

3.3: 35 percent / pyridine

With lithium aluminium tetrahydride; copper(2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline])(triflate)2; dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether; 1.1: Cycloaddition / 2.1: Reduction / 2.2: Acetylation / 3.1: Reduction / 3.2: Oxidation / 3.3: Acetylation;
DOI:10.1021/jo9918596