{(3aS,4R,6S,7R,7aR)-4-[(R)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {(3aS,4R,6S,7R,7aR)-4-[(R)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl ester
• CAS No.: 87256-64-2
• Molecular Formula: C₂₆H₃₇NO₁₁
• Molecular Weight: 539.58

Synonyms:

Chemical Property of {(3aS,4R,6S,7R,7aR)-4-[(R)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(3aS,4R,6S,7R,7aR)-4-[(R)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl ester

There total 16 articles about {(3aS,4R,6S,7R,7aR)-4-[(R)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl 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:

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose (26775-14-4) → {(3aS,4R,6S,7R,7aR)-4-[(S)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl ester (87256-64-2,87305-36-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / aq. acetic acid

3: 98 percent / NaI

4: 43 percent / sodium nitrile

5: 2.) KF / 2.) acetonitrile

6: acetic anhydride, pyridene / CHCl₃

7: NaBH₄

With potassium fluoride; sodium tetrahydroborate; sodium nitrile; acetic anhydride; acetic acid; sodium iodide; phenazopyridine hydrochloride; In chloroform;

DOI:10.1246/cl.1983.819

Reference yield:

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose (26775-14-4) → {(3aS,4R,6S,7R,7aR)-4-[(R)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl ester (87256-64-2,87305-36-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / aq. acetic acid

3: 98 percent / NaI

4: 43 percent / sodium nitrile

5: 2.) KF / 2.) acetonitrile

6: acetic anhydride, pyridene / CHCl₃

7: NaBH₄

With potassium fluoride; sodium tetrahydroborate; sodium nitrile; acetic anhydride; acetic acid; sodium iodide; phenazopyridine hydrochloride; In chloroform;

DOI:10.1246/cl.1983.819

Reference yield:

3'-O-acetyl-1',2'-O-isopropylidene-5',6'-diol-α-D-allofuranose (51433-05-7) → {(3aS,4R,6S,7R,7aR)-4-[(S)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl ester (87256-64-2,87305-36-0)

Guidance literature:

Multi-step reaction with 7 steps

2: 98 percent / NaI

3: 43 percent / sodium nitrile

4: 2.) KF / 2.) acetonitrile

5: acetic anhydride, pyridene / CHCl₃

6: NaBH₄

With potassium fluoride; sodium tetrahydroborate; sodium nitrile; acetic anhydride; sodium iodide; phenazopyridine hydrochloride; In chloroform;

DOI:10.1246/cl.1983.819

upstream raw materials:

Acetic acid (3aR,5R,6R,6aR)-5-[2-((3aS,4R,6S,7R,7aR)-7-benzyloxycarbonylamino-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-nitro-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose

3'-O-acetyl-1',2'-O-isopropylidene-5',6'-diol-α-D-allofuranose

3-O-acetyl-5-deoxy-1,2-O-isopropylidene-5-nitro-α-D-ribofuranose

Downstream raw materials:

Acetic acid (2R,3S,4R)-2-[(R)-1-acetoxy-2-((2R,3R,4R,5R,6S)-5-benzyloxycarbonylamino-3,4-dihydroxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-4,5-dihydroxy-tetrahydro-furan-3-yl ester

1-<(11S)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-11-O-methyl-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil

methyl 3,4,7,9,10,11-hexa-O-acetyl-2-(benzyloxycarbonyl)amino-2,6-dideoxy-β-L-allo-D-galacto-undecodialdofuranose-(11,8)-pyranoside-(1,5)

Acetic acid (2R,3S,4R)-2-[(S)-1-acetoxy-2-((2R,3R,4R,5R,6S)-5-benzyloxycarbonylamino-3,4-dihydroxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-4,5-dihydroxy-tetrahydro-furan-3-yl ester

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