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

Base Information

Chemical Name:(R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid
CAS No.:220033-97-6
Molecular Formula:C₂₀H₂₉N₃O₅
Molecular Weight:391.467
Hs Code.:

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

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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

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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

There total 10 articles about (R)-2-((2R,3S,5R,6S)-6-Azidomethyl-3-benzyloxy-5-isobutoxy-tetrahydro-pyran-2-yl)-propionic acid 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:

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

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

Guidance literature:: Multi-step reaction with 10 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

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;
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

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

Guidance literature:: Multi-step reaction with 9 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

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;
DOI:10.1016/S0960-894X(98)00575-7

Reference yield:

: 2-O-Benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-L-glucopyranoside

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

Guidance literature:: Multi-step reaction with 2 steps

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

2: aq. LiOH / methanol

With lithium hydroxide; sodium methylate; In methanol;
DOI:10.1016/S0960-894X(98)00575-7