(2R,4R,5R,6S)-2-Azidomethyl-4,5-bis-benzyloxy-6-methoxy-dihydro-pyran-3-one

Base Information

Chemical Name:(2R,4R,5R,6S)-2-Azidomethyl-4,5-bis-benzyloxy-6-methoxy-dihydro-pyran-3-one
CAS No.:389065-64-9
Molecular Formula:C₂₁H₂₃N₃O₅
Molecular Weight:397.431
Hs Code.:

Synonyms:(2R,4R,5R,6S)-2-Azidomethyl-4,5-bis-benzyloxy-6-methoxy-dihydro-pyran-3-one

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Chemical Property of (2R,4R,5R,6S)-2-Azidomethyl-4,5-bis-benzyloxy-6-methoxy-dihydro-pyran-3-one

Chemical Property:

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Technology Process of (2R,4R,5R,6S)-2-Azidomethyl-4,5-bis-benzyloxy-6-methoxy-dihydro-pyran-3-one

There total 6 articles about (2R,4R,5R,6S)-2-Azidomethyl-4,5-bis-benzyloxy-6-methoxy-dihydro-pyran-3-one 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:

: 54522-58-6
methyl 6-azido-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside

: 389065-64-9
(2R,4R,5R,6S)-2-Azidomethyl-4,5-bis-benzyloxy-6-methoxy-dihydro-pyran-3-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -65 - -45 ℃; for 0.5h;
DOI:10.1016/S0040-4039(01)01472-1

Reference yield:

: 54522-57-5
methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside

: 389065-64-9
(2R,4R,5R,6S)-2-Azidomethyl-4,5-bis-benzyloxy-6-methoxy-dihydro-pyran-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: 6.41 g / NaN₃ / dimethylformamide / 80 °C

2: (COCl)2; DMSO; DIPEA / CH₂Cl₂ / -78 - -10 °C

With sodium azide; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; 2: Swern oxidation;
DOI:10.1021/jo035290r

Reference yield:

: 97-30-3
methyl-alpha-D-glucopyranoside

: 389065-64-9
(2R,4R,5R,6S)-2-Azidomethyl-4,5-bis-benzyloxy-6-methoxy-dihydro-pyran-3-one

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / PPTS / dimethylformamide

2: 95 percent / NaH; TBAI / tetrahydrofuran

3: 99 percent / TsOH*H₂O / methanol

4: pyridine / 0 - 20 °C

5: 6.41 g / NaN₃ / dimethylformamide / 80 °C

6: (COCl)2; DMSO; DIPEA / CH₂Cl₂ / -78 - -10 °C

With pyridine; sodium azide; oxalyl dichloride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 6: Swern oxidation;
DOI:10.1021/jo035290r