(S)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl ester

Base Information

Chemical Name:(S)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl ester
CAS No.:857860-14-1
Molecular Formula:C₃₂H₃₇N₃O₈
Molecular Weight:591.661
Hs Code.:

Synonyms:(S)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl ester

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Chemical Property of (S)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl ester

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Technology Process of (S)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl ester

There total 7 articles about (S)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl 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%

: 857860-12-9
(2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde

: 141-78-6
ethyl acetate

: 857860-13-0
(R)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl ester

: 857860-14-1
(S)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl ester

Guidance literature:: ethyl acetate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde; In tetrahydrofuran; hexane; at -78 - 20 ℃;
DOI:10.1021/ol0508577

Reference yield:

: (2R,3R,4S,5S)-2-Azido-6-methylene-tetrahydro-pyran-3,4,5-triol

: 857860-14-1
(S)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1.3 g / sodium hydride / dimethylformamide / 3 h / 20 °C

2.1: 98 percent / 1,1,1-trifluoroacetone; Oxone; sodium hydrogen carbonate / sodium EDTA / acetonitrile; H₂O / 1.5 h / 0 - 20 °C

3.1: 100 percent / camphorsulfonic acid / 0.17 h / 20 °C

4.1: 46 percent / N-methylmorpholine N-oxide / tetra-n-propyl-ammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

5.1: butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 16 percent / tetrahydrofuran; hexane / -78 - 20 °C

With Oxone; n-butyllithium; 1,1,1-trifluoro-2-propanone; camphor-10-sulfonic acid; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; diisopropylamine; tetrapropylammonium perruthennate; ethylene diamine tetraacetic acid tetrasodium salt; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol0508577

Reference yield:

: 857860-08-3
(5R,6R,7R,8S)-5-Azido-6,7,8-tris-benzyloxy-1,4-dioxa-spiro[2.5]octane

: 857860-14-1
(S)-3-((2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 100 percent / camphorsulfonic acid / 0.17 h / 20 °C

2.1: 46 percent / N-methylmorpholine N-oxide / tetra-n-propyl-ammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

3.1: butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 16 percent / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; camphor-10-sulfonic acid; 4-methylmorpholine N-oxide; diisopropylamine; tetrapropylammonium perruthennate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0508577