[(2R,3R,6S)-6-((R)-1-Benzyloxycarbonylamino-ethyl)-2-((1R,2R,3S,4R,6R)-6-benzyloxycarbonylamino-4-fluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(2R,3R,6S)-6-((R)-1-Benzyloxycarbonylamino-ethyl)-2-((1R,2R,3S,4R,6R)-6-benzyloxycarbonylamino-4-fluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester
• CAS No.: 83865-98-9
• Molecular Formula: C₃₈H₄₇FN₄O₉
• Molecular Weight: 722.811

Synonyms:

Chemical Property of [(2R,3R,6S)-6-((R)-1-Benzyloxycarbonylamino-ethyl)-2-((1R,2R,3S,4R,6R)-6-benzyloxycarbonylamino-4-fluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [(2R,3R,6S)-6-((R)-1-Benzyloxycarbonylamino-ethyl)-2-((1R,2R,3S,4R,6R)-6-benzyloxycarbonylamino-4-fluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

There total 6 articles about [(2R,3R,6S)-6-((R)-1-Benzyloxycarbonylamino-ethyl)-2-((1R,2R,3S,4R,6R)-6-benzyloxycarbonylamino-4-fluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-tetrahydro-pyran-3-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:

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-epi-3-fluoro-3-de(methoxy)sporaricin B (83865-97-8,83916-88-5) → [(2R,3R,6S)-6-((R)-1-Benzyloxycarbonylamino-ethyl)-2-((1R,2R,3S,4R,6R)-6-benzyloxycarbonylamino-4-fluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (83865-98-9,87039-06-3)

Guidance literature:

With barium dihydroxide; In 1,4-dioxane; water; at 80 ℃; for 1.5h; Yield given; Heating;

DOI:10.1016/0008-6215(83)88117-8

Reference yield:

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-fluoro-3-de(methoxy)sporaricin B (83865-97-8,83916-88-5) → [(2R,3R,6S)-6-((R)-1-Benzyloxycarbonylamino-ethyl)-2-((1R,2R,3S,4S,6R)-6-benzyloxycarbonylamino-4-fluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (83865-98-9,87039-06-3)

Guidance literature:

With barium dihydroxide; In 1,4-dioxane; water; at 80 ℃; for 1.5h; Heating;

DOI:10.1016/0008-6215(83)88117-8

Reference yield:

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-de(methoxy)-3-oxo-sporaricin B (83866-00-6) → [(2R,3R,6S)-6-((R)-1-Benzyloxycarbonylamino-ethyl)-2-((1R,2R,3S,4S,6R)-6-benzyloxycarbonylamino-4-fluoro-2-hydroxy-3-methylamino-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (83865-98-9,87039-06-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 742 mg / sodium borohydride / methanol / 2 h / Ambient temperature

2: 68 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 1.) -15 deg C, 15 min; 2.) r.t., 30 min

3: 0.25 M barium hydroxide / dioxane; H₂O / 1.5 h / 80 °C / Heating

With barium dihydroxide; sodium tetrahydroborate; diethylamino-sulfur trifluoride; In 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1016/0008-6215(83)88117-8

upstream raw materials:

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-fluoro-3-de(methoxy)sporaricin B

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-de(methoxy)-3-oxo-sporaricin B

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-epi-3-de(O-methyl)sporaricin B

1,2',6'-tris(N-benzyloxycarbonyl)-4-N,5-O-carbonyl-3-de(O-methyl)sporaricin B

Downstream raw materials:

3-fluoro-3-de(methoxy)sporaricin A hydrochloride

3-epi-3-fluoro-3-de(methoxy)sporaricin A hydrochloride

1,2',6'-tris(N-benzyloxycarbonyl)-4-N-(N-benzyloxycarbonylglycyl)-3-epi-3-fluoro-3-de(methoxy)sporaricin B

1,2',6'-tris(N-benzyloxycarbonyl)-4-N-(N-benzyloxycarbonylglycyl)-3-fluoro-3-de(methoxy)sporaricin B

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