methyl 6-azido-2-benzyloxycarbonylamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside

Base Information

Chemical Name:methyl 6-azido-2-benzyloxycarbonylamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside
CAS No.:99239-14-2
Molecular Formula:C₁₆H₂₂N₄O₄
Molecular Weight:334.375
Hs Code.:

Synonyms:methyl 6-azido-2-benzyloxycarbonylamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside

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Chemical Property of methyl 6-azido-2-benzyloxycarbonylamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside

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Technology Process of methyl 6-azido-2-benzyloxycarbonylamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside

There total 14 articles about methyl 6-azido-2-benzyloxycarbonylamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside 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: 94.0%

: 99239-13-1
methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-6-O-(methylsulfonyl)-α-D-ribo-heptopyranoside

: 99239-14-2
methyl 6-azido-2-benzyloxycarbonylamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 1.5h;
DOI:10.1016/0008-6215(86)85023-6

Reference yield:

: 99239-04-0
methyl 2-benzyloxycarbonylamino-2,3,4-trideoxy-6-O-trityl-α-D-erythro-hex-3-enopyranoside

: 99239-14-2
methyl 6-azido-2-benzyloxycarbonylamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 3.74 g / H₂ / 10percent Pd-C / ethyl acetate; acetic acid / 6 h / 760 Torr / Ambient temperature

2: 78 percent / Et₃N / CH₂Cl₂ / 1.) 2 h, room temp., 2.) overnight, room temp., 3.) 5 h, reflux

3: 81 percent / aq. acetic acid / 0.5 h / 100 °C

4: 78 percent / Me₂SO, DCC, pyridine, CF₃COOH / 1.) room temp., overnight, 2.) 40 deg C, 30 min

5: 1.) THF, -20 - -15 deg C, 20 min, 2.) pyridine, room temp., 1 d

6: 53 percent / dimethylformamide / 18 h / Heating

7: H₂NNH₂*H₂O / ethanol / 2 h / Heating

8: M NaOH / acetone; H₂O / 0.5 h / Ambient temperature

9: KOH / methanol / 2 h / Ambient temperature

10: 99 percent / pyridine / Ambient temperature

11: 94 percent / NaN₃ / dimethylformamide / 1.5 h / 100 °C

With pyridine; potassium hydroxide; sodium hydroxide; sodium azide; hydrogen; hydrazine hydrate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In pyridine; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0008-6215(86)85023-6

Reference yield:

: 99239-02-8
methyl 2-benzyloxycarbonylamino-2-deoxy-6-O-trityl-α-D-glucopyranoside

: 99239-14-2
methyl 6-azido-2-benzyloxycarbonylamino-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside

Guidance literature:: Multi-step reaction with 13 steps

1: 81 percent / pyridine / Ambient temperature

2: 67 percent / Zn, NaI / dimethylformamide / 5.5 h / 95 °C

3: 3.74 g / H₂ / 10percent Pd-C / ethyl acetate; acetic acid / 6 h / 760 Torr / Ambient temperature

4: 78 percent / Et₃N / CH₂Cl₂ / 1.) 2 h, room temp., 2.) overnight, room temp., 3.) 5 h, reflux

5: 81 percent / aq. acetic acid / 0.5 h / 100 °C

6: 78 percent / Me₂SO, DCC, pyridine, CF₃COOH / 1.) room temp., overnight, 2.) 40 deg C, 30 min

7: 1.) THF, -20 - -15 deg C, 20 min, 2.) pyridine, room temp., 1 d

8: 53 percent / dimethylformamide / 18 h / Heating

9: H₂NNH₂*H₂O / ethanol / 2 h / Heating

10: M NaOH / acetone; H₂O / 0.5 h / Ambient temperature

11: KOH / methanol / 2 h / Ambient temperature

12: 99 percent / pyridine / Ambient temperature

13: 94 percent / NaN₃ / dimethylformamide / 1.5 h / 100 °C

With pyridine; potassium hydroxide; sodium hydroxide; sodium azide; hydrogen; hydrazine hydrate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium iodide; zinc; palladium on activated charcoal; In pyridine; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0008-6215(86)85023-6