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

Base Information

• Chemical Name: [(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,3R,4S,5R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester
• CAS No.: 113886-44-5
• Molecular Formula: C₃₀H₃₈N₄O₁₂
• Molecular Weight: 646.651
• Mol file: 113886-44-5.mol

Synonyms:

Chemical Property of [(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,3R,4S,5R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,3R,4S,5R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

There total 2 articles about [(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,3R,4S,5R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-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: 13.0%

nitromethane (75-52-5) + Acetic acid (3S,4R,5R,6S)-2-acetoxy-4-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yl ester (113886-50-3,113974-85-9) → [(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,4R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (113886-44-5,113973-81-2,113973-84-5,113974-86-0,113974-88-2) + [(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,3R,4S,5R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (113886-44-5,113973-81-2,113973-84-5,113974-86-0,113974-88-2)

Guidance literature:

With sodium methylate; In methanol; at 26 ℃; for 48h;

DOI:10.1248/cpb.35.2136

Reference yield: 13.0%

nitromethane (75-52-5) + Acetic acid (3S,4R,5R,6S)-2-acetoxy-4-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yl ester (113886-50-3,113974-85-9) → [(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,4R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (113886-44-5,113973-81-2,113973-84-5,113974-86-0,113974-88-2) + [(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,3R,4S,5R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (113886-44-5,113973-81-2,113973-84-5,113974-86-0,113974-88-2)

Guidance literature:

With sodium methylate; In methanol; at 26 ℃; for 48h;

DOI:10.1248/cpb.35.2136

Reference yield:

[(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,4R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (113886-44-5,113973-81-2,113973-84-5,113974-86-0,113974-88-2) → dibecacin (34493-98-6)

Guidance literature:

Multi-step reaction with 11 steps

1: d-10-camphorsulfonic acid / dimethylformamide

2: NaOAc

3: 56 percent / NaBH₄ / aq. ethanol / 0.5 h / 5 °C

4: H₂ / Raney Ni (T-4) / 760 Torr

5: Na₂CO₃ / H₂O; dioxane

6: 80 percent aq. AcOH / 60 °C

7: 77 percent / AgClO₄, sym-collidine / benzene; dioxane / 0.5 h / 24 °C

8: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H₂O / 1.) acetone, H₂O; 2.) dioxane, H₂O

9: methanol

10: H₂ / 5 percent Pd/C / acetic acid / 1900 Torr

11: 70 percent / 80 percent aq. NH₂NH₂ / 72 h / 100 °C

With 2,4,6-trimethyl-pyridine; barium dihydroxide; sodium tetrahydroborate; Dowex 1*2(OH- form); camphor-10-sulfonic acid; hydrogen; sodium acetate; silver perchlorate; sodium carbonate; hydrazine hydrate; acetic acid; palladium on activated charcoal; Raney Ni (T-4); In 1,4-dioxane; methanol; ethanol; water; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.35.2136

upstream raw materials:

nitromethane

Acetic acid (3S,4R,5R,6S)-2-acetoxy-4-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yl ester

Downstream raw materials:

dibecacin

{(1R,2S,3R,4R,5S)-4-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-ethoxycarbonylamino-tetrahydro-pyran-2-yloxy]-5-ethoxycarbonylamino-2,3-dihydroxy-cyclohexyl}-carbamic acid ethyl ester

penta-N-acetyldibekacin

Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester