8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one

Base Information

• Chemical Name: 8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one
• CAS No.: 162992-52-1
• Molecular Formula: C₂₈H₂₉NO₅
• Molecular Weight: 459.542
• Mol file: 162992-52-1.mol

Synonyms:8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one

Chemical Property of 8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one

There total 2 articles about 8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one 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: 88.0%

benzyl bromide (100-39-0) + 8(R)-(Hydroxymethyl)-6(R),7(R)-dihydroxy-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one (162895-65-0) → 8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one (162992-52-1)

Guidance literature:

With sodium hydride; potassium iodide; In N,N-dimethyl-formamide; for 12h; Ambient temperature;

DOI:10.1021/jo00111a007

Reference yield:

2,5-anhydro-2,5-imino-D-glucitol (132295-44-4) → 8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one (162992-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 10percent aq. NaHCO₃ / toluene / 1 h

2: 88 percent / NaH, KI / dimethylformamide / 12 h / Ambient temperature

With sodium hydride; sodium hydrogencarbonate; potassium iodide; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00111a007

Reference yield: 90.0%

8(R)-<(Benzyloxy)methyl>-6(R),7(R)-bis(benzyloxy)-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one (162992-52-1) → 5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine (162992-53-2)

Guidance literature:

With potassium hydroxide; In ethylene glycol; at 100 ℃; for 24h;

DOI:10.1021/jo00111a007

upstream raw materials:

benzyl bromide

8(R)-(Hydroxymethyl)-6(R),7(R)-dihydroxy-5(S)-3-oxa-1-azabicyclo<3.3.0>octan-2-one

2,5-anhydro-2,5-imino-D-glucitol

Downstream raw materials:

5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine

5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-formyl-N-methylpyrrolidine

5(R)-<(Benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)-N-methylpyrrolidine

N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(hydroxymethyl)pyrrolidine