methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-α-D-ribo-heptopyranoside

Base Information

• Chemical Name: methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-α-D-ribo-heptopyranoside
• CAS No.: 99239-12-0
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• Mol file: 99239-12-0.mol

Synonyms:

Chemical Property of methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-α-D-ribo-heptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-α-D-ribo-heptopyranoside

There total 12 articles about methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-α-D-ribo-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:

methyl 2-benzyloxycarbonylamino-2,3,4-trideoxy-6-O-trityl-α-D-erythro-hex-3-enopyranoside (99239-04-0) → methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-α-D-ribo-heptopyranoside (99239-12-0)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; potassium hydroxide; sodium hydroxide; hydrogen; hydrazine hydrate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0008-6215(86)85023-6

Reference yield:

methyl 2-benzyloxycarbonylamino-2-deoxy-6-O-trityl-α-D-glucopyranoside (99239-02-8) → methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-α-D-ribo-heptopyranoside (99239-12-0)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; potassium hydroxide; sodium hydroxide; 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

Reference yield:

methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-bis-O-(methylsulfonyl)-6-O-trityl-α-D-glucopyranoside (99239-03-9) → methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-α-D-ribo-heptopyranoside (99239-12-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 67 percent / Zn, NaI / dimethylformamide / 5.5 h / 95 °C

2: 3.74 g / H₂ / 10percent Pd-C / ethyl acetate; acetic acid / 6 h / 760 Torr / Ambient temperature

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

4: 81 percent / aq. acetic acid / 0.5 h / 100 °C

5: 78 percent / Me₂SO, DCC, pyridine, CF₃COOH / 1.) room temp., overnight, 2.) 40 deg C, 30 min

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

7: 53 percent / dimethylformamide / 18 h / Heating

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

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

10: KOH / methanol / 2 h / Ambient temperature

With pyridine; potassium hydroxide; sodium hydroxide; hydrogen; hydrazine hydrate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium iodide; zinc; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0008-6215(86)85023-6

upstream raw materials:

benzyl chloroformate

methyl 2,3,4-trideoxy-2-phthalimido-α-D-erythro-hexodialdo-1,5-pyranoside

methyl 2,3,4-trideoxy-2-phthalimido-α-D-glucopyranoside

methyl 2-amino-2,3,4-trideoxy-6-O-trityl-α-D-glucopyranoside

Downstream raw materials:

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

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

methyl 2,6-bis(benzyloxycarbonylamino)-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside