Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide

Base Information

Chemical Name:Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide
CAS No.:89872-85-5
Molecular Formula:C₁₉H₂₄O₆
Molecular Weight:348.396
Hs Code.:

Synonyms:Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide

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Chemical Property of Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide

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Technology Process of Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide

There total 8 articles about Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide 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%

: 89872-84-4
(2R,4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 77-76-9
2,2-dimethoxy-propane

: 89872-85-5
Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide

Guidance literature:: With toluene-4-sulfonic acid; In benzene; for 4h; Ambient temperature;
DOI:10.1021/jo00187a010

Reference yield: 72.0%

: 116-11-0
2-Methoxypropene

: 89872-84-4
(4aR,6S,8R,8aS)-7-[2-Hydroxy-eth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 89872-85-5,111056-63-4
methyl 4,6-O-benzylidene-2-C-<(E)-2-hydroxyethylidene>-3,2¹-O-isopropylidene-α-D-arabino-hexopyranoside

Guidance literature:: With pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1016/S0008-6215(00)90006-5

Reference yield:

: 112711-35-0
methyl 3-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-[(R)-phenylmethylene]-α-D-glucopyranoside

: 89872-85-5
Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / dimethylsulfoxide, trifluoracetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

2: 90 percent / acetonitrile / Heating

3: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

5: 80 percent / p-toluenesulfonic acid / benzene / 4 h / Ambient temperature

With lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; benzene;
DOI:10.1021/jo00187a010