3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

Base Information

Chemical Name:3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose
CAS No.:85315-74-8
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

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Chemical Property of 3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

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Technology Process of 3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

There total 16 articles about 3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose 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: 83.0%

: 3-deoxy-3-C-benzyloxymethyl-5,6-di-p-toluene-sulfonyl-oxy-1,2-O-isopropylidene-α-D-allofuranose

: 85315-74-8
3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

Guidance literature:: With sodium iodide; zinc; In N,N-dimethyl-formamide; for 4h; Heating;
DOI:10.1016/j.tet.2007.01.037

Reference yield: 79.0%

: 314061-33-1
Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester

: 85315-74-8
3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

Guidance literature:: With sodium iodide; In 1,2-dimethoxyethane; Heating;
DOI:10.1016/S0040-4039(00)01437-4

Reference yield:

: 69832-48-0
((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

: 85315-74-8
3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / Bu₄NI / aq. NaOH

2: 100 percent / aq. ACOH / 40 °C

3: 82 percent / Et₃N / CH₂Cl₂

4: 79 percent / NaI / 1,2-dimethoxy-ethane / Heating

With tetra-(n-butyl)ammonium iodide; acetic acid; triethylamine; sodium iodide; In sodium hydroxide; 1,2-dimethoxyethane; dichloromethane; 1: Etherification / 2: Hydrolysis / 3: mesylation / 4: Elimination;
DOI:10.1016/S0040-4039(00)01437-4