(2S,3S,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Base Information

Chemical Name:(2S,3S,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde
CAS No.:614752-30-6
Molecular Formula:C₂₁H₂₄O₅
Molecular Weight:356.419
Hs Code.:

Synonyms:(2S,3S,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

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Chemical Property of (2S,3S,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Chemical Property:

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Technology Process of (2S,3S,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

There total 6 articles about (2S,3S,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-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:

: 145149-85-5
Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside

: 614752-30-6
(2S,3S,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃;

With triethylamine; In dichloromethane; at -78 - 0 ℃; Further stages.;
DOI:10.1021/jo026163i

Reference yield:

: 675128-77-5
methyl 3,4-di-O-benzyl-2-deoxy-D-arabino-hexopyraboside

: 614752-30-6
(2S,3S,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

: (2S,3S,4R,6R)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -45 - 20 ℃; Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(03)01103-7

Reference yield:

: 61-58-5,13299-15-5,13299-16-6,14215-77-1,14215-78-2,20789-85-9,23568-30-1,25494-04-6,34339-39-4,34339-40-7,34339-46-3,34339-47-4,114717-20-3,114717-21-4,137491-75-9,137491-76-0
2-deoxy-D-arabino-hexopyranose

: 614752-30-6
(2S,3S,4R,6S)-3,4-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / AcCl / 4 h / 23 °C

2.1: 70 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: 99 percent / NaH; n-Bu₄NI / dimethylformamide / 16 h / 20 °C

4.1: 95 percent / n-Bu₄NF / tetrahydrofuran / 6 h / 20 °C

5.1: DMSO; oxalyl chloride / CH₂Cl₂ / -78 °C

5.2: Et₃N / CH₂Cl₂ / -78 - 0 °C

With 1H-imidazole; oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; acetyl chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern oxidation;
DOI:10.1021/jo026163i