(2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde

Base Information

Chemical Name:(2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde
CAS No.:359765-22-3
Molecular Formula:C₂₅H₃₀O₇
Molecular Weight:442.509
Hs Code.:

Synonyms:(2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde

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Chemical Property of (2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde

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Technology Process of (2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde

There total 5 articles about (2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde 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: 76.5%

: 359765-21-2
methyl 5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

: 359765-22-3
(2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde

Guidance literature:: With swern reagent;
DOI:10.1016/S0008-6215(01)00103-3

Reference yield:

: 100-39-0
benzyl bromide

: 359765-22-3
(2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 80.5 percent / NaH / dimethylformamide / 3 h / -10 - 20 °C

2: 67.8 percent / 1,4-diazabicyclo[2.2.2]octane / Wilkinson's catalyst / ethanol; hexane; H₂O / 4 h / Heating

3: 76.5 percent / Swern reagent

With 1,4-diaza-bicyclo[2.2.2]octane; swern reagent; sodium hydride; Wilkinson's catalyst; In ethanol; hexane; water; N,N-dimethyl-formamide; 3: Swern oxidation;
DOI:10.1016/S0008-6215(01)00103-3

Reference yield:

: 201788-59-2
methyl 5-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,4-furanoside

: 359765-22-3
(2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 59.7 percent / magnesium / tetrahydrofuran / 14 h / -30 - 20 °C

2: 80.5 percent / NaH / dimethylformamide / 3 h / -10 - 20 °C

3: 67.8 percent / 1,4-diazabicyclo[2.2.2]octane / Wilkinson's catalyst / ethanol; hexane; H₂O / 4 h / Heating

4: 76.5 percent / Swern reagent

With 1,4-diaza-bicyclo[2.2.2]octane; swern reagent; sodium hydride; magnesium; Wilkinson's catalyst; In tetrahydrofuran; ethanol; hexane; water; N,N-dimethyl-formamide; 4: Swern oxidation;
DOI:10.1016/S0008-6215(01)00103-3