{(4aR,6S,7R,8R,8aS)-8-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-methoxy-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)-8-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester
• CAS No.: 113892-26-5
• Molecular Formula: C₃₈H₄₅N₃O₁₁
• Molecular Weight: 719.789
• Mol file: 113892-26-5.mol

Synonyms:

Chemical Property of {(4aR,6S,7R,8R,8aS)-8-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-methoxy-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)-8-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester

There total 9 articles about {(4aR,6S,7R,8R,8aS)-8-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-methoxy-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:

benzyl chloroformate (501-53-1,94274-21-2) → {(4aR,6S,7R,8R,8aS)-8-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester (113892-26-5)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; sodium azide; sodium hydrogencarbonate; acetic acid; zinc; In 1,4-dioxane; water; N,N-dimethyl-formamide;

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) → {(4aR,6S,7R,8R,8aS)-8-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester (113892-26-5)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 2,4,6-trimethyl-pyridine; sodium azide; Dowex 1*2(OH₁-); silver perchlorate; sodium hydrogencarbonate; acetic acid; zinc; In 1,4-dioxane; 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 → {(4aR,6S,7R,8R,8aS)-8-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester (113892-26-5)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; sodium azide; sodium hydrogencarbonate; acetic acid; zinc; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.35.2136

upstream raw materials:

acetic anhydride

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:

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

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