[(4aR,6S,7R,8R,8aS)-6-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(4aR,6S,7R,8R,8aS)-6-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester
• CAS No.: 85464-59-1
• Molecular Formula: C₃₅H₃₉N₃O₁₄
• Molecular Weight: 725.706

Synonyms:

Chemical Property of [(4aR,6S,7R,8R,8aS)-6-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4aR,6S,7R,8R,8aS)-6-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

There total 12 articles about [(4aR,6S,7R,8R,8aS)-6-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-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: 84.0%

[(2S,3R,4R,5S,6R)-2-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (85502-93-8) + benzaldehyde (100-52-7) → [(4aR,6S,7R,8R,8aS)-6-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester (85464-59-1)

Guidance literature:

With zinc(II) chloride; for 2.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)85695-6

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-5-benzyloxycarbonylamino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy)-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester → [(4aR,6S,7R,8R,8aS)-6-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester (85464-59-1)

Guidance literature:

Multi-step reaction with 4 steps

1: CrO₃, H₂SO₄ / 3 h / Ambient temperature

2: benzene; pyridine / 3.5 h / Heating

3: 22 percent / 1percent NaOMe / methanol / 36 h / Ambient temperature

4: 84 percent / ZnCl₂ / 2.5 h / Ambient temperature

With chromium(VI) oxide; sulfuric acid; sodium methylate; zinc(II) chloride; In pyridine; methanol; benzene;

DOI:10.1016/S0040-4039(00)85695-6

Reference yield:

Acetic acid (3S,4R,5R,6S)-2-acetoxy-5-benzyloxycarbonylamino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy)-6-methoxy-tetrahydro-pyran-3-yl ester (85464-58-0,85551-12-8) → [(4aR,6S,7R,8R,8aS)-6-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester (85464-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 22 percent / 1percent NaOMe / methanol / 36 h / Ambient temperature

2: 84 percent / ZnCl₂ / 2.5 h / Ambient temperature

With sodium methylate; zinc(II) chloride; In methanol;

DOI:10.1016/S0040-4039(00)85695-6

upstream raw materials:

[(2S,3R,4R,5S,6R)-2-((1R,2S,3S,4R,5S,6R)-2-Benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

benzaldehyde

Acetic acid (3S,4R,5R,6S)-2-acetoxy-5-benzyloxycarbonylamino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy)-6-methoxy-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5S,6R)-3-benzyloxycarbonylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-4-yl ester

Downstream raw materials:

C₄₁H₄₇N₃O₁₃

C₄₅H₅₁N₃O₁₆

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