(S)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-3-amino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:(S)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-3-amino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
CAS No.:192444-76-1
Molecular Formula:C₃₀H₄₉NO₇
Molecular Weight:535.722
Hs Code.:

Synonyms:(S)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-3-amino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

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Chemical Property of (S)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-3-amino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

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Technology Process of (S)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-3-amino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

There total 4 articles about (S)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-3-amino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl 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: 98.0%

: 172371-10-7
allyl 3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 192444-76-1
(S)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-3-amino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With zinc copper; acetic acid; at 20 ℃; for 0.5h;
DOI:10.1246/bcsj.70.1441

Reference yield:

: 97562-24-8
allyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 192444-76-1
(S)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-3-amino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 92 percent / AcOH / H₂O / 0.17 h / 95 °C

3: 98 percent / zinc-copper couple; AcOH / 0.5 h / 20 °C

With dmap; zinc copper; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; water; 1: Esterification / 2: Hydrolysis / 3: dealkoxycarbonylation;
DOI:10.1246/bcsj.70.1441

Reference yield:

: (S)-3-(benzyloxy)tetradecanoic acid

: 192444-76-1
(S)-3-Benzyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-3-amino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 92 percent / AcOH / H₂O / 0.17 h / 95 °C

3: 98 percent / zinc-copper couple; AcOH / 0.5 h / 20 °C

With dmap; zinc copper; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; water; 1: Esterification / 2: Hydrolysis / 3: dealkoxycarbonylation;
DOI:10.1246/bcsj.70.1441