(3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
• CAS No.: 158780-50-8
• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.396
• Mol file: 158780-50-8.mol

Synonyms:(3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Chemical Property of (3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

There total 3 articles about (3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid allyl ester (158780-49-5) → (3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (158780-50-8) + (3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (158780-51-9)

Guidance literature:

With chloro-trimethyl-silane; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) HMPA, THF, -100 deg C to RT;

DOI:10.1016/S0040-4039(00)76001-1

Reference yield:

methanol (67-56-1) + {Allyloxy-[(3aR,6S,6aS)-6-benzyloxy-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-(4Z)-ylidene]-methoxy}-trimethyl-silane → (3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (158780-50-8) + (3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (158780-51-9)

Guidance literature:

With tetrabutyl ammonium fluoride; diazomethyl-trimethyl-silane; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, r.t., 1 h, 2.) benzene, hexane, r.t., 1 h;

DOI:10.1055/s-1999-3686

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + allyl alcohol (107-18-6) + benzyl 2,3-O-(1-methylethylidene)-α-D-lyxofuranosiduronic acid chloride (96150-86-6) → (3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (158780-50-8) + (3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (158780-51-9)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

upstream raw materials:

diazomethane

(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid allyl ester

allyl alcohol

benzyl 2,3-O-(1-methylethylidene)-α-D-lyxofuranosiduronic acid chloride

Downstream raw materials:

phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2-propenyl)-α-D-lyxofuranoside

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2-acetyloxy-3-phenylthiopropyl)-α-D-lyxofuranoside