(1R,3aR,7aR,7bR)-1-Benzyloxy-7-oxo-3,3a,5,7,7a,7b-hexahydro-1H-pentaleno[1,6-cd]pyran-4,4-dicarboxylic acid dimethyl ester

Base Information

Chemical Name:(1R,3aR,7aR,7bR)-1-Benzyloxy-7-oxo-3,3a,5,7,7a,7b-hexahydro-1H-pentaleno[1,6-cd]pyran-4,4-dicarboxylic acid dimethyl ester
CAS No.:176590-00-4
Molecular Formula:C₂₁H₂₂O₇
Molecular Weight:386.401
Hs Code.:

Synonyms:(1R,3aR,7aR,7bR)-1-Benzyloxy-7-oxo-3,3a,5,7,7a,7b-hexahydro-1H-pentaleno[1,6-cd]pyran-4,4-dicarboxylic acid dimethyl ester

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Chemical Property of (1R,3aR,7aR,7bR)-1-Benzyloxy-7-oxo-3,3a,5,7,7a,7b-hexahydro-1H-pentaleno[1,6-cd]pyran-4,4-dicarboxylic acid dimethyl ester

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Technology Process of (1R,3aR,7aR,7bR)-1-Benzyloxy-7-oxo-3,3a,5,7,7a,7b-hexahydro-1H-pentaleno[1,6-cd]pyran-4,4-dicarboxylic acid dimethyl ester

There total 5 articles about (1R,3aR,7aR,7bR)-1-Benzyloxy-7-oxo-3,3a,5,7,7a,7b-hexahydro-1H-pentaleno[1,6-cd]pyran-4,4-dicarboxylic acid dimethyl 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:

: 71978-99-9
benzyl 4-O-acetyl-2,3-dideoxy-α-D-glycero-pent-2-enopyranoside

: 176590-00-4
(1R,3aR,7aR,7bR)-1-Benzyloxy-7-oxo-3,3a,5,7,7a,7b-hexahydro-1H-pentaleno[1,6-cd]pyran-4,4-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.24 g / triethylamine / methanol; H₂O / 4 h / Ambient temperature

2: 94 percent / p-toluenesulfonyl chloride, pyridine / 50 °C / 3-4 h

3: 1.) NaH, 2.) triphenylphosphine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / 1.) THF, 0 deg C, 20 min, 2.) THF, 0 deg C, 1 h

4: 2.) DMSO / 1.) benzene, room temperature, 2-3 h, 2.) 50 deg C, 24 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; In methanol; water;
DOI:10.1021/jo951298s

Reference yield:

: benzyl 2,3-anhydro-4-O-acetyl-α-D-ribopyranoside

: 176590-00-4
(1R,3aR,7aR,7bR)-1-Benzyloxy-7-oxo-3,3a,5,7,7a,7b-hexahydro-1H-pentaleno[1,6-cd]pyran-4,4-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) sodium iodide, sodium acetate, acetic acid, 2.) POCl₃, pyridine / 1.) acetone, reflux, 4-5 h, 2.) -40 -> 0 deg C

2: 1.24 g / triethylamine / methanol; H₂O / 4 h / Ambient temperature

3: 94 percent / p-toluenesulfonyl chloride, pyridine / 50 °C / 3-4 h

4: 1.) NaH, 2.) triphenylphosphine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / 1.) THF, 0 deg C, 20 min, 2.) THF, 0 deg C, 1 h

5: 2.) DMSO / 1.) benzene, room temperature, 2-3 h, 2.) 50 deg C, 24 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium acetate; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; sodium iodide; trichlorophosphate; In methanol; water;
DOI:10.1021/jo951298s

Reference yield:

: 176589-99-4
2-((3R,6R)-6-Benzyloxy-3,6-dihydro-2H-pyran-3-yl)-2-prop-2-ynyl-malonic acid dimethyl ester

: 176590-00-4
(1R,3aR,7aR,7bR)-1-Benzyloxy-7-oxo-3,3a,5,7,7a,7b-hexahydro-1H-pentaleno[1,6-cd]pyran-4,4-dicarboxylic acid dimethyl ester

Guidance literature:: With dimethyl sulfoxide; Yield given. Multistep reaction; 1.) benzene, room temperature, 2-3 h, 2.) 50 deg C, 24 h;
DOI:10.1021/jo951298s