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

Base Information

• Chemical Name: (3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid allyl ester
• CAS No.: 158780-49-5
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.369
• Mol file: 158780-49-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid allyl 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: 90.0%

allyl alcohol (107-18-6) + benzyl 2,3-O-(1-methylethylidene)-α-D-lyxofuranosiduronic acid chloride (96150-86-6) → (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)

Guidance literature:

With dmap; In dichloromethane;

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

Reference yield:

phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside (54469-08-8,74912-00-8,74912-01-9,20689-02-5) → (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)

Guidance literature:

Multi-step reaction with 4 steps

1: conc. HCl / methanol; H₂O

2: 1.) NaIO₄, 2.) AgNO₃, KOH / 1.) H₂O, MeOH

3: oxalyl chloride, DMF / benzene / 2 h / Ambient temperature

4: 4-dimethylaminopyridine / CH₂Cl₂ / 2 h

With hydrogenchloride; dmap; potassium hydroxide; sodium periodate; oxalyl dichloride; silver nitrate; N,N-dimethyl-formamide; In methanol; dichloromethane; water; benzene;

Reference yield:

1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose (74912-02-0,79940-48-0,94118-99-7,20689-03-6) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaIO₄, 2.) AgNO₃, KOH / 1.) H₂O, MeOH

2: oxalyl chloride, DMF / benzene / 2 h / Ambient temperature

3: 4-dimethylaminopyridine / CH₂Cl₂ / 2 h

With dmap; potassium hydroxide; sodium periodate; oxalyl dichloride; silver nitrate; N,N-dimethyl-formamide; In dichloromethane; benzene;

upstream raw materials:

allyl alcohol

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

phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside

1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose

Downstream raw materials:

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

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