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

Base Information

• Chemical Name: (3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid
• CAS No.: 96150-84-4
• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.304
• Mol file: 96150-84-4.mol

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

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

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

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 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%

benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside (102919-04-0,102854-75-1) → (3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (96150-84-4)

Guidance literature:

With potassium hydroxide; silver nitrate; In ethanol; at 20 ℃; for 1.5h;

DOI:10.1021/ja056714x

Reference yield: 33.0%

1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose (74912-02-0,79940-48-0,94118-99-7,20689-03-6) → (benzyl 2,3-O-isopropylidene-α-D-mannofuranosid)uronic acid (1400695-53-5) + (3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (96150-84-4)

Guidance literature:

With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In aq. phosphate buffer; acetonitrile; at 20 ℃; for 24h; pH=6.8; Inert atmosphere;

DOI:10.1021/ol3021429

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 (96150-84-4)

Guidance literature:

With potassium hydroxide; sodium periodate; silver nitrate; Yield given. Multistep reaction; 1.) MeOH, H₂O, 1 h 75 min; 2.) H₂O, EtOH, 9.5 h;

DOI:10.1021/ja00297a038

upstream raw materials:

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

benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside

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

benzyl chloride

Downstream raw materials:

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

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

(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2R,3S,4R)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester

(3aR,4S,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S)-3-benzyloxy-2-methoxy-5-methylene-tetrahydro-pyran-4-yl ester