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

Base Information

• Chemical Name: 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
• CAS No.: 113886-50-3
• Molecular Formula: C₃₄H₄₃N₃O₁₃
• Molecular Weight: 701.728
• Mol file: 113886-50-3.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 13 articles about 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 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:

benzyl chloroformate (501-53-1,94274-21-2) → 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)

Guidance literature:

Multi-step reaction with 9 steps

1: NaHCO₃ / dioxane; H₂O / 2 °C

2: pyridine

3: NaN₃ / dimethylformamide / 80 °C

4: Zn, 90 percent aq. acetic acid / dimethylformamide / 2 °C

5: pyridine

6: 60 percent HClO₄ / acetone

7: pyridine

8: 4-dimethylaminopyridine / pyridine

9: 1.) BF₃-Et₂O; 2.) Jones reagent; 3.) Pb(OAc)4 / 1.) THF; 3.) benzene, pyridine, 1.5 h, reflux

With pyridine; lead(IV) acetate; dmap; sodium azide; perchloric acid; jones reagent; boron trifluoride diethyl etherate; sodium hydrogencarbonate; acetic acid; zinc; In 1,4-dioxane; pyridine; water; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.35.2136

Reference yield:

Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester (113886-85-4) → 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)

Guidance literature:

Multi-step reaction with 11 steps

1: 68 percent / AgClO₄, sym-collidine / benzene; dioxane / 0.25 h / 27 °C

2: Dowex 1*2(OH₁-) / acetone; H₂O / 25 °C

3: NaHCO₃ / dioxane; H₂O / 2 °C

4: pyridine

5: NaN₃ / dimethylformamide / 80 °C

6: Zn, 90 percent aq. acetic acid / dimethylformamide / 2 °C

7: pyridine

8: 60 percent HClO₄ / acetone

9: pyridine

10: 4-dimethylaminopyridine / pyridine

11: 1.) BF₃-Et₂O; 2.) Jones reagent; 3.) Pb(OAc)4 / 1.) THF; 3.) benzene, pyridine, 1.5 h, reflux

With pyridine; 2,4,6-trimethyl-pyridine; lead(IV) acetate; dmap; sodium azide; perchloric acid; jones reagent; Dowex 1*2(OH₁-); boron trifluoride diethyl etherate; silver perchlorate; sodium hydrogencarbonate; acetic acid; zinc; In 1,4-dioxane; pyridine; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1248/cpb.35.2136

Reference yield:

[(4aR,6S,7R,8R,8aS)-8-((2R,3R,6S)-3-Amino-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester → 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)

Guidance literature:

Multi-step reaction with 9 steps

1: NaHCO₃ / dioxane; H₂O / 2 °C

2: pyridine

3: NaN₃ / dimethylformamide / 80 °C

4: Zn, 90 percent aq. acetic acid / dimethylformamide / 2 °C

5: pyridine

6: 60 percent HClO₄ / acetone

7: pyridine

8: 4-dimethylaminopyridine / pyridine

9: 1.) BF₃-Et₂O; 2.) Jones reagent; 3.) Pb(OAc)4 / 1.) THF; 3.) benzene, pyridine, 1.5 h, reflux

With pyridine; lead(IV) acetate; dmap; sodium azide; perchloric acid; jones reagent; boron trifluoride diethyl etherate; sodium hydrogencarbonate; acetic acid; zinc; In 1,4-dioxane; pyridine; water; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.35.2136

upstream raw materials:

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

benzyl chloroformate

Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester

[(4aR,6S,7R,8R,8aS)-8-((2R,3R,6S)-3-Benzyloxycarbonylamino-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

Downstream raw materials:

[(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

[(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