1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone

Base Information

Chemical Name:1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone
CAS No.:106445-50-5
Molecular Formula:C₃₅H₃₆O₆
Molecular Weight:552.667
Hs Code.:

Synonyms:

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Chemical Property of 1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone

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Technology Process of 1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone

There total 9 articles about 1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone 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: 18.3%

: 106445-46-9
(S)-2-Amino-1-((2R,3S,4S,5S,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanol

: 106445-50-5
1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone

: 106445-48-1
benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With acetic acid; sodium nitrite; In 1,4-dioxane; water; 0 deg C, RT, 5 h;
DOI:10.1016/0008-6215(86)80013-1

Reference yield:

: 77455-30-2
benzyl 6-O-triphenylmethyl-α-D-mannopyranoside

: 106445-50-5
1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone

Guidance literature:: Multi-step reaction with 6 steps

1: sodium hydroxide / dimethylsulfoxide / 1.5 h / Ambient temperature

2: trifluoroacetic acid / dioxane; methanol / Heating

3: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -60 °C

4: 34 percent / pyridine / 0 deg C, 2 h, RT, 24 h

5: lithium aluminum hydride / various solvent(s) / 0.17 h / 0 °C

6: 18.3 percent / sodium nitrite, 0.2M acetic acid / dioxane; H₂O / 0 deg C, RT, 5 h

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; acetic acid; dimethyl sulfoxide; trifluoroacetic acid; sodium nitrite; In 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1016/0008-6215(86)80013-1

Reference yield:

: 15548-45-5
(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

: 106445-50-5
1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / pyridine, 4-dimethylaminopyridine / 72 h / 40 °C

2: sodium hydroxide / dimethylsulfoxide / 1.5 h / Ambient temperature

3: trifluoroacetic acid / dioxane; methanol / Heating

4: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -60 °C

5: 34 percent / pyridine / 0 deg C, 2 h, RT, 24 h

6: lithium aluminum hydride / various solvent(s) / 0.17 h / 0 °C

7: 18.3 percent / sodium nitrite, 0.2M acetic acid / dioxane; H₂O / 0 deg C, RT, 5 h

With pyridine; dmap; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; acetic acid; dimethyl sulfoxide; trifluoroacetic acid; sodium nitrite; In 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1016/0008-6215(86)80013-1