Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 214918-34-0
• Molecular Formula: C₃₂H₃₆NO₁₁P
• Molecular Weight: 641.612

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 15 articles about Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl 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:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester (214918-34-0)

Guidance literature:

Multi-step reaction with 14 steps

1: NaBH₄ / ethanol

2: pyridine

3: NaN₃, 15-crown-5

4: LiAlH₄ / diethyl ether

5: Na₂CO₃

6: 60percent aq. AcOH / 60 °C

7: pyridine

8: NaI / acetone

9: NaBH₄ / bis-(2-methoxy-ethyl) ether

10: 0.1 N aq. HCl

11: pyridine

12: NH₂NH₂, AcOH

13: 1H-tetrazole

14: m-CPBA

With pyridine; 1H-tetrazole; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; 15-crown-5; sodium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; hydrazine; In diethyl ether; ethanol; diethylene glycol dimethyl ether; acetone;

DOI:10.1021/ja9815881

Reference yield:

1,2,5,6-di-O-isopropylidene-3-O-(p-toluenesulfonyl)-α-D-allofuranose (3253-75-6,13964-21-1,19131-06-7,23344-48-1,26597-75-1,28140-21-8) → Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester (214918-34-0)

Guidance literature:

Multi-step reaction with 12 steps

1: NaN₃, 15-crown-5

2: LiAlH₄ / diethyl ether

3: Na₂CO₃

4: 60percent aq. AcOH / 60 °C

5: pyridine

6: NaI / acetone

7: NaBH₄ / bis-(2-methoxy-ethyl) ether

8: 0.1 N aq. HCl

9: pyridine

10: NH₂NH₂, AcOH

11: 1H-tetrazole

12: m-CPBA

With pyridine; 1H-tetrazole; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; 15-crown-5; sodium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; hydrazine; In diethyl ether; diethylene glycol dimethyl ether; acetone;

DOI:10.1021/ja9815881

Reference yield:

3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose (13964-23-3) → Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester (214918-34-0)

Guidance literature:

Multi-step reaction with 11 steps

1: LiAlH₄ / diethyl ether

2: Na₂CO₃

3: 60percent aq. AcOH / 60 °C

4: pyridine

5: NaI / acetone

6: NaBH₄ / bis-(2-methoxy-ethyl) ether

7: 0.1 N aq. HCl

8: pyridine

9: NH₂NH₂, AcOH

10: 1H-tetrazole

11: m-CPBA

With pyridine; 1H-tetrazole; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; hydrazine; In diethyl ether; diethylene glycol dimethyl ether; acetone;

DOI:10.1021/ja9815881

upstream raw materials:

(1,2:5,6)-di-O-isopropylidene-D-gulose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose

1,2,5,6-di-O-isopropylidene-3-O-(p-toluenesulfonyl)-α-D-allofuranose

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