1-azido-1,2-dideoxy-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(methoxymethyl)-2-methylene-D-threo-pentitol

Base Information

Chemical Name:1-azido-1,2-dideoxy-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(methoxymethyl)-2-methylene-D-threo-pentitol
CAS No.:260804-83-9
Molecular Formula:C₂₆H₃₇N₃O₅Si
Molecular Weight:499.682
Hs Code.:

Synonyms:1-azido-1,2-dideoxy-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(methoxymethyl)-2-methylene-D-threo-pentitol

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Chemical Property of 1-azido-1,2-dideoxy-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(methoxymethyl)-2-methylene-D-threo-pentitol

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Technology Process of 1-azido-1,2-dideoxy-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(methoxymethyl)-2-methylene-D-threo-pentitol

There total 9 articles about 1-azido-1,2-dideoxy-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(methoxymethyl)-2-methylene-D-threo-pentitol 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:

: Methanesulfonic acid (3R,4R)-5-(tert-butyl-diphenyl-silanyloxy)-3,4-bis-methoxymethoxy-2-methylene-pentyl ester

: 260804-83-9
1-azido-1,2-dideoxy-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(methoxymethyl)-2-methylene-D-threo-pentitol

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1021/jo982448c

Reference yield:

: 260804-76-0
5,6-O-isopropylidene-2,3-di-O-methoxymethyl-L-galactono-γ-lactone

: 260804-83-9
1-azido-1,2-dideoxy-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(methoxymethyl)-2-methylene-D-threo-pentitol

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

2: 99.7 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 1 h / 20 °C

3: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4: 96 percent / tetrahydrofuran / -78 - 20 °C

5: 99 percent / aq. AcOH / 20 °C

6: 3.73 g / NaIO₄ / acetonitrile; H₂O / 1 h / 20 °C

7: 3.4 g / CeCl₃; NaBH₄ / methanol / 1 h / 20 °C

8: pyridine / 1 h / 20 °C

9: 25 g / NaN₃ / dimethylformamide / 1 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; sodium azide; cerium(III) chloride; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Reduction / 2: Substitution / 3: Oxidation / 4: Wittig reaction / 5: Hydrolysis / 6: Oxidation / 7: Luche reduction / 8: Substitution / 9: Substitution;
DOI:10.1021/jo982448c

Reference yield:

: 260804-77-1
1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-D-galactitol

: 260804-83-9
1-azido-1,2-dideoxy-6-O-(tert-butyldiphenylsilyl)-3,4-di-O-(methoxymethyl)-2-methylene-D-threo-pentitol

Guidance literature:: Multi-step reaction with 8 steps

1: 99.7 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 1 h / 20 °C

2: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

3: 96 percent / tetrahydrofuran / -78 - 20 °C

4: 99 percent / aq. AcOH / 20 °C

5: 3.73 g / NaIO₄ / acetonitrile; H₂O / 1 h / 20 °C

6: 3.4 g / CeCl₃; NaBH₄ / methanol / 1 h / 20 °C

7: pyridine / 1 h / 20 °C

8: 25 g / NaN₃ / dimethylformamide / 1 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium azide; cerium(III) chloride; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Oxidation / 3: Wittig reaction / 4: Hydrolysis / 5: Oxidation / 6: Luche reduction / 7: Substitution / 8: Substitution;
DOI:10.1021/jo982448c