benzyl (2S,3S)-4-(1,3-dioxan-2-yl)-2-amino-3-((tert-butyldimethylsilyl)oxy)butanoate

Base Information

Chemical Name:benzyl (2S,3S)-4-(1,3-dioxan-2-yl)-2-amino-3-((tert-butyldimethylsilyl)oxy)butanoate
CAS No.:213539-59-4
Molecular Formula:C₂₁H₃₅NO₅Si
Molecular Weight:409.598
Hs Code.:

Synonyms:benzyl (2S,3S)-4-(1,3-dioxan-2-yl)-2-amino-3-((tert-butyldimethylsilyl)oxy)butanoate

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Chemical Property of benzyl (2S,3S)-4-(1,3-dioxan-2-yl)-2-amino-3-((tert-butyldimethylsilyl)oxy)butanoate

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Technology Process of benzyl (2S,3S)-4-(1,3-dioxan-2-yl)-2-amino-3-((tert-butyldimethylsilyl)oxy)butanoate

There total 9 articles about benzyl (2S,3S)-4-(1,3-dioxan-2-yl)-2-amino-3-((tert-butyldimethylsilyl)oxy)butanoate 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: 98.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 213539-58-3
benzyl (2S,3S)‐2‐amino‐4‐(1,3‐dioxan‐2‐yl)‐3‐hydroxybutanoate

: 213539-59-4
benzyl (2S,3S)-4-(1,3-dioxan-2-yl)-2-amino-3-((tert-butyldimethylsilyl)oxy)butanoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 3.5h;
DOI:10.1021/jo980765d

Reference yield:

: 100-39-0
benzyl bromide

: 213539-59-4
benzyl (2S,3S)-4-(1,3-dioxan-2-yl)-2-amino-3-((tert-butyldimethylsilyl)oxy)butanoate

Guidance literature:: Multi-step reaction with 6 steps

1: dimethylformamide / 23 °C

2: 80 percent / AD mix α, methane sulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 4 °C

3: 68 percent / Et₃N / CH₂Cl₂ / 12 h / 4 °C

4: 87 percent / NaN₃ / dimethylformamide / 14 h / 50 °C

5: 93 percent / PPh₃ / tetrahydrofuran; H₂O / 50 °C

6: 98 percent / 2,6-lutidine / CH₂Cl₂ / 3.5 h / 0 °C

With 2,6-dimethylpyridine; AD-mix-α; sodium azide; methanesulfonamide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo980765d

Reference yield:

: 79012-29-6
2‐(1,3‐dioxan‐2‐yl)acetaldehyde

: 213539-59-4
benzyl (2S,3S)-4-(1,3-dioxan-2-yl)-2-amino-3-((tert-butyldimethylsilyl)oxy)butanoate

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / t-BuOK / methanol / 1 h / 23 °C

2: LiOH*H₂O / tetrahydrofuran; H₂O / 18 h / 23 °C

3: dimethylformamide / 23 °C

4: 80 percent / AD mix α, methane sulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 4 °C

5: 68 percent / Et₃N / CH₂Cl₂ / 12 h / 4 °C

6: 87 percent / NaN₃ / dimethylformamide / 14 h / 50 °C

7: 93 percent / PPh₃ / tetrahydrofuran; H₂O / 50 °C

8: 98 percent / 2,6-lutidine / CH₂Cl₂ / 3.5 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; AD-mix-α; sodium azide; methanesulfonamide; potassium tert-butylate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo980765d