(-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride

Base Information

Chemical Name:(-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride
CAS No.:153215-67-9
Molecular Formula:C₁₅H₁₇ClO₅
Molecular Weight:312.75
Hs Code.:

Synonyms:(-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride

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Chemical Property of (-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride

Chemical Property:

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Technology Process of (-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride

There total 8 articles about (-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride 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: 92.0%

: 39682-04-7
(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

: 153215-67-9
(-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride

Guidance literature:: With oxalyl dichloride; In dichloromethane; for 5h; Heating;
DOI:10.1016/j.tet.2007.06.073

Reference yield:

: 153237-94-6
Acetic acid (S)-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-((4R,5R,6R)-4,5-bis-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-methyl ester

: 153215-67-9
(-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride

Guidance literature:: With oxalyl dichloride; In dichloromethane; at 0 ℃; for 1h;

Reference yield:

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 153215-67-9
(-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / AgNO₃; aq. KOH / 1 h / 20 °C

2: 92 percent / oxalyl chloride / CH₂Cl₂ / 5 h / Heating

With potassium hydroxide; oxalyl dichloride; silver nitrate; In dichloromethane;
DOI:10.1016/j.tet.2007.06.073