2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose

Base Information

Chemical Name:2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose
CAS No.:263243-26-1
Molecular Formula:C₃₄H₃₅NO₆
Molecular Weight:553.655
Hs Code.:

Synonyms:2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose

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Chemical Property of 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose

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Technology Process of 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose

There total 10 articles about 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose 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: 95.0%

: 161512-13-6
2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-D-arabinitol

: 263243-26-1
2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 0.666667h;
DOI:10.1016/S0008-6215(99)00253-0

Reference yield:

: 5-azido-5-deoxy-D-arabinofuranose

: 263243-26-1
2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / NaBH₄ / methanol / 0.5 h / 20 °C

2: 83 percent / pyridine / 48 h / 20 °C

3: 95 percent / NaH / dimethylformamide / 3.5 h / 0 - 20 °C

4: 63 percent / AcOH 70 percent / H₂O / 4 h / 60 °C

5: LiAlH₄ / tetrahydrofuran / 20 °C

6: 95 percent / tetrahydrofuran / 0 °C

7: 95 percent / Me₂SO; (COCl)2; Et₃N / CH₂Cl₂ / 0.67 h / -78 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Reduction / 2: tritylation / 3: benzylation / 4: Elimination / 5: Reduction / 6: Substitution / 7: Swern oxidation, hemiaminal construction;
DOI:10.1016/S0008-6215(99)00253-0

Reference yield:

: 55287-20-2
1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose

: 263243-26-1
2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinose

Guidance literature:: Multi-step reaction with 10 steps

1: 79 percent / pyridine / 0.33 h / 0 - 20 °C

2: 68 percent / NaN₃ / dimethylsulfoxide / 24 h / 60 °C

3: 100 percent / NaOMe / methanol / 5 h / sonication

4: 100 percent / NaBH₄ / methanol / 0.5 h / 20 °C

5: 83 percent / pyridine / 48 h / 20 °C

6: 95 percent / NaH / dimethylformamide / 3.5 h / 0 - 20 °C

7: 63 percent / AcOH 70 percent / H₂O / 4 h / 60 °C

8: LiAlH₄ / tetrahydrofuran / 20 °C

9: 95 percent / tetrahydrofuran / 0 °C

10: 95 percent / Me₂SO; (COCl)2; Et₃N / CH₂Cl₂ / 0.67 h / -78 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; sodium methylate; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: mesylation / 2: Substitution / 3: Deacetylation / 4: Reduction / 5: tritylation / 6: benzylation / 7: Elimination / 8: Reduction / 9: Substitution / 10: Swern oxidation, hemiaminal construction;
DOI:10.1016/S0008-6215(99)00253-0