(2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid
CAS No.:177213-15-9
Molecular Formula:C₃₃H₃₉NO₈
Molecular Weight:577.675
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

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Chemical Property of (2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

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Technology Process of (2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

There total 7 articles about (2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid 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: 54.0%

: 24424-99-5
di-tert-butyl dicarbonate

: (2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid

: 177213-15-9
(2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

Guidance literature:: With lithium hydroxide; at 20 ℃; for 12h;
DOI:10.1016/j.tet.2006.05.080

Reference yield:

: 57039-38-0
(2R,3R,4S,5S,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-carboxylate

: 177213-15-9
(2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 83 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: Ag₂O / dimethylformamide / 20 h / 20 °C

2.2: 7.60 g / acetic acid / H₂O; tetrahydrofuran / 15 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

4.1: 81 percent / sodium azide / dimethylformamide / 12 h / 20 °C

5.1: 82 percent / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 12 h / 20 °C

6.1: hydrogen / Lindlar catalyst / methanol / 3 h / 20 °C

7.1: 54 percent / LiOH*H₂O / 12 h / 20 °C

With pyridine; 1H-imidazole; lithium hydroxide; sodium azide; hydrogen; silver(l) oxide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2006.05.080

Reference yield:

: 177213-12-6
(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate

: 177213-15-9
(2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 12 h / 20 °C

2: 81 percent / sodium azide / dimethylformamide / 12 h / 20 °C

3: 82 percent / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 12 h / 20 °C

4: hydrogen / Lindlar catalyst / methanol / 3 h / 20 °C

5: 54 percent / LiOH*H₂O / 12 h / 20 °C

With pyridine; lithium hydroxide; sodium azide; hydrogen; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2006.05.080