[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Base Information

Chemical Name:[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester
CAS No.:918416-18-9
Molecular Formula:C₃₉H₅₂N₂O₉
Molecular Weight:692.85
Hs Code.:

[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

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Chemical Property of [(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

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Technology Process of [(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

There total 7 articles about [(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic 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:

: [(2R,3R,4R,5R,6R)-2-((S)-1-Amino-2-hydroxy-ethyl)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

: 24424-99-5
di-tert-butyl dicarbonate

: 918416-18-9
[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1016/j.tetlet.2006.10.024

Reference yield:

: 852620-03-2
((2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

: 918416-18-9
[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: NMO*H₂O; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 30 h

2: 94 mg / Et₃N / CH₂Cl₂ / 8 h

3: Et₃N / CH₂Cl₂ / 12 h / 20 °C

4: 73 mg / HCl / CHCl₃ / 2 h / 0 °C

5: NaN₃ / dimethylformamide / 6 h / 80 °C

6: triphenylphosphine; water / tetrahydrofuran / 10 h / 20 °C

7: 107 mg / Et₃N / CH₂Cl₂ / 3 h / 20 °C

With hydrogenchloride; osmium(VIII) oxide; sodium azide; water; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2006.10.024

Reference yield:

: [(2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(1,2-dihydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

: 918416-18-9
[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 94 mg / Et₃N / CH₂Cl₂ / 8 h

2: Et₃N / CH₂Cl₂ / 12 h / 20 °C

3: 73 mg / HCl / CHCl₃ / 2 h / 0 °C

4: NaN₃ / dimethylformamide / 6 h / 80 °C

5: triphenylphosphine; water / tetrahydrofuran / 10 h / 20 °C

6: 107 mg / Et₃N / CH₂Cl₂ / 3 h / 20 °C

With hydrogenchloride; sodium azide; water; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2006.10.024