2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol

Base Information

Chemical Name:2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol
CAS No.:202460-05-7
Molecular Formula:C₂₉H₃₅N₃O₄Si
Molecular Weight:517.7
Hs Code.:

Synonyms:2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol

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Chemical Property of 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol

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Technology Process of 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol

There total 7 articles about 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol 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 (1S,2S,3S)-3-azido-4-(tert-butyl-diphenyl-silanyloxy)-1-hydroxymethyl-2-(4-methoxy-benzyloxy)-butyl ester

: 202460-05-7
2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol

Guidance literature:: With sodium methylate; In methanol; at 0 - 20 ℃; for 4h;
DOI:10.1246/bcsj.71.259

Reference yield:

: 202460-00-2
2-azido-2-deoxy-4,5-O-isopropylidene-3-O-(4-methoxybenzyl)-L-mannitol

: 202460-05-7
2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol

Guidance literature:: Multi-step reaction with 8 steps

1: acetic acid / H₂O / 2 h / 50 °C

2: 3.48 g / p-toluenesulfonic acid monohydrate / 5 h / 20 °C

3: 100 percent / imidazole / dimethylformamide / 10.2 h / 0 - 20 °C

4: 100 percent / triethylamine / CH₂Cl₂ / 1.17 h / 0 - 20 °C

5: 75 percent / acetic acid / H₂O / 17 h / 50 °C

6: lead(IV) acetate / benzene / 0.5 h / 20 °C

7: NaBH₄ / methanol / 1 h / 0 - 20 °C

8: 768 mg / sodium methoxide / methanol / 4 h / 0 - 20 °C

With 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; sodium methylate; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: Hydrolysis / 2: Cyclization / 3: silylation / 4: mesylation / 5: Hydrolysis / 6: Oxidation / 7: Reduction / 8: Cyclization;
DOI:10.1246/bcsj.71.259

Reference yield:

: (2S,3S,4S,5S)-5-Azido-4-(4-methoxy-benzyloxy)-hexane-1,2,3,6-tetraol

: 202460-05-7
2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol

Guidance literature:: Multi-step reaction with 7 steps

1: 3.48 g / p-toluenesulfonic acid monohydrate / 5 h / 20 °C

2: 100 percent / imidazole / dimethylformamide / 10.2 h / 0 - 20 °C

3: 100 percent / triethylamine / CH₂Cl₂ / 1.17 h / 0 - 20 °C

4: 75 percent / acetic acid / H₂O / 17 h / 50 °C

5: lead(IV) acetate / benzene / 0.5 h / 20 °C

6: NaBH₄ / methanol / 1 h / 0 - 20 °C

7: 768 mg / sodium methoxide / methanol / 4 h / 0 - 20 °C

With 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; sodium methylate; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: Cyclization / 2: silylation / 3: mesylation / 4: Hydrolysis / 5: Oxidation / 6: Reduction / 7: Cyclization;
DOI:10.1246/bcsj.71.259