(3aS,4S,6S,7aS)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

Base Information

Chemical Name:(3aS,4S,6S,7aS)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde
CAS No.:871706-63-7
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

Synonyms:(3aS,4S,6S,7aS)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

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Chemical Property of (3aS,4S,6S,7aS)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

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Technology Process of (3aS,4S,6S,7aS)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

There total 5 articles about (3aS,4S,6S,7aS)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde 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:

: 871706-62-6
benzyl 4-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside

: 871706-63-7
(3aS,4S,6S,7aS)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 0.583333h;
DOI:10.1021/ol051936l

Reference yield:

: 871706-61-5
benzyl 4-deoxy-2,3-O-isopropylidene-6-O-pivaloyl-α-D-mannopyranoside

: 871706-63-7
(3aS,4S,6S,7aS)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / sodium methoxide; MeOH / 2 h / 20 °C

2: 570 mg / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.58 h / -78 - 20 °C

With methanol; oxalyl dichloride; sodium methylate; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/ol051936l

Reference yield:

: 871706-59-1
benzyl 2,3-O-isopropylidene-6-O-pivaloyl-α-D-mannopyranoside

: 871706-63-7
(3aS,4S,6S,7aS)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: imidazole; NaH / tetrahydrofuran / 0.67 h / 20 °C

1.2: tetrahydrofuran / 0.5 h / 20 °C

2.1: 97 percent / 2,2'-azobisisobutyronitrile; Bu₃SnH / toluene / 2.17 h / Heating

3.1: 85 percent / sodium methoxide; MeOH / 2 h / 20 °C

4.1: 570 mg / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.58 h / -78 - 20 °C

With 1H-imidazole; methanol; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ol051936l