(R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

Base Information

Chemical Name:(R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester
CAS No.:259726-49-3
Molecular Formula:C₂₄H₃₇N₃O₅
Molecular Weight:447.575
Hs Code.:

Synonyms:(R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

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Chemical Property of (R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

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Technology Process of (R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

There total 11 articles about (R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid tert-butyl 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: 80.0%

: 220033-97-6
(R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid

: 36805-97-7
N,N-dimethylformamide di-tert-butyl acetal

: 259726-49-3
(R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

Guidance literature:: In toluene; at 85 ℃;
DOI:10.1016/S0960-894X(98)00575-7

Reference yield:

: 259726-43-7
(2R,3S,5R,6S)-2-tert-Butoxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

: 259726-49-3
(R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: PPTS

2: 93 percent / NaH, TBAI / tetrahydrofuran

3: DIBAL / CH₂Cl₂

4: Et₃N, DMAP / CH₂Cl₂

5: NaN₃ / dimethylformamide / 90 °C

6: 74 percent / DDQ / CH₂Cl₂; H₂O

7: 86 percent / NaH, TBAI / tetrahydrofuran

8: 72 percent / 70percent aq. AcOH

9: 2.) NaOMe / 1.) MeCN, reflux, 2.) MeOH

10: aq. LiOH / methanol

11: 80 percent / toluene / 85 °C

With dmap; lithium hydroxide; sodium azide; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0960-894X(98)00575-7

Reference yield:

: 220033-94-3
1-O-tert-Butyl-4,6-O-p-methoxybenzylidene-3-deoxy-β-L-gluco-pyranoside

: 259726-49-3
(R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / NaH, TBAI / tetrahydrofuran

2: DIBAL / CH₂Cl₂

3: Et₃N, DMAP / CH₂Cl₂

4: NaN₃ / dimethylformamide / 90 °C

5: 74 percent / DDQ / CH₂Cl₂; H₂O

6: 86 percent / NaH, TBAI / tetrahydrofuran

7: 72 percent / 70percent aq. AcOH

8: 2.) NaOMe / 1.) MeCN, reflux, 2.) MeOH

9: aq. LiOH / methanol

10: 80 percent / toluene / 85 °C

With dmap; lithium hydroxide; sodium azide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0960-894X(98)00575-7