N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide

Base Information

Chemical Name:N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide
CAS No.:124820-33-3
Molecular Formula:C₃₂H₃₉NO₆S
Molecular Weight:565.731
Hs Code.:

Synonyms:N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide

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Chemical Property of N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide

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Technology Process of N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide

There total 7 articles about N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide 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: 80.0%

: 124780-60-5
Methyl 2,3,4-Tris-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-1-thio-D-erythro-α-D-galacto-octopyranoside

: 108-24-7
acetic anhydride

: 124820-33-3
N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide

Guidance literature:: With methanol; potassium hydroxide; ethylene glycol; 1) reflux, 96h, 2) r.t., 3h;
DOI:10.1021/jo00292a044

Reference yield:

: 124780-66-1
methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside

: 124820-33-3
N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / Ambient temperature

3: imidazole, NaH / dimethylformamide / 1) 12h, 0 deg C, 2) 48h, r.t.

4: 100 percent / NaH / dimethylformamide / 12 h / Ambient temperature

5: 100 percent / sulfuric acid / -20 - 0 °C

6: 75 percent / trimethylsilyl trifluoromethanesulfonate / CCl₄ / 3 h / Heating

7: 80 percent / 1) KOH, ethylene glycol, 2) MeOH / 1) reflux, 96h, 2) r.t., 3h

With pyridine; 1H-imidazole; methanol; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium hydride; ethylene glycol; In tetrachloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00292a044

Reference yield:

: 124780-55-8
(2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-((2R,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-ol

: 124820-33-3
N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole, NaH / dimethylformamide / 1) 12h, 0 deg C, 2) 48h, r.t.

2: 100 percent / NaH / dimethylformamide / 12 h / Ambient temperature

3: 100 percent / sulfuric acid / -20 - 0 °C

4: 75 percent / trimethylsilyl trifluoromethanesulfonate / CCl₄ / 3 h / Heating

5: 80 percent / 1) KOH, ethylene glycol, 2) MeOH / 1) reflux, 96h, 2) r.t., 3h

With 1H-imidazole; methanol; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium hydride; ethylene glycol; In tetrachloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00292a044