Acetic acid (3R,4R,6S)-3,4-diacetoxy-6-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-yl ester

Base Information

Chemical Name:Acetic acid (3R,4R,6S)-3,4-diacetoxy-6-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-yl ester
CAS No.:824411-70-3
Molecular Formula:C₂₁H₂₇NO₁₀
Molecular Weight:453.446
Hs Code.:

Synonyms:Acetic acid (3R,4R,6S)-3,4-diacetoxy-6-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-yl ester

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Chemical Property of Acetic acid (3R,4R,6S)-3,4-diacetoxy-6-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-yl ester

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Technology Process of Acetic acid (3R,4R,6S)-3,4-diacetoxy-6-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-yl ester

There total 8 articles about Acetic acid (3R,4R,6S)-3,4-diacetoxy-6-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-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: 91.0%

: 824411-69-0
(R)-2,2-Dimethyl-4-((2S,4R,5R)-4,5,6-triacetoxy-tetrahydro-pyran-2-yl)-oxazolidine-3-carboxylic acid benzyl ester

: 824411-70-3
Acetic acid (3R,4R,6S)-3,4-diacetoxy-6-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-yl ester

Guidance literature:: With formic acid; In dichloromethane; at 0 ℃; for 20h;
DOI:10.1021/jo048586l

Reference yield:

: 824411-63-4
(6S)-6-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-5,6-dihydropyran-2-one

: 824411-70-3
Acetic acid (3R,4R,6S)-3,4-diacetoxy-6-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / NMO; OsO₄; H₂O / acetone; toluene / 2 h / 20 °C

2: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

3: 1.27 g / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

4: 91 percent / aq. formic acid / CH₂Cl₂ / 20 h / 0 °C

With pyridine; dmap; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; water; diisobutylaluminium hydride; In dichloromethane; acetone; toluene;
DOI:10.1021/jo048586l

Reference yield:

: 824411-61-2
(4R)-4-[(1'S)-1-acryloyloxy-but-3-enyl]-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidine

: 824411-70-3
Acetic acid (3R,4R,6S)-3,4-diacetoxy-6-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / [bis(tricyclohexylphosphine)benzylideneruthenium(IV)]Cl₂ / CH₂Cl₂ / 24 h / Heating

2: 81 percent / NMO; OsO₄; H₂O / acetone; toluene / 2 h / 20 °C

3: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

4: 1.27 g / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

5: 91 percent / aq. formic acid / CH₂Cl₂ / 20 h / 0 °C

With pyridine; Grubbs catalyst first generation; dmap; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; water; diisobutylaluminium hydride; In dichloromethane; acetone; toluene;
DOI:10.1021/jo048586l