[(4aR,6R,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy)-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(4aR,6R,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy)-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester
• CAS No.: 76951-79-6
• Molecular Formula: C₄₁H₅₀N₂O₁₃
• Molecular Weight: 778.854
• Mol file: 76951-79-6.mol

Synonyms:

Chemical Property of [(4aR,6R,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy)-8-benzyloxy-2,2-dimethyl-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,6R,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy)-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

There total 4 articles about [(4aR,6R,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy)-8-benzyloxy-2,2-dimethyl-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: 88.0%

C38H46N2O13 (76951-78-5) + 2,2-dimethoxy-propane (77-76-9) → [(4aR,6R,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy)-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester (76951-79-6)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1246/cl.1980.1373

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → [(4aR,6R,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy)-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester (76951-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / tetrahydrofuran

2: 75 percent / conc. aq. ammonia, ethanol (1:2) / 4.5 h / 50 °C

3: 88 percent / p-toluenesulfonic acid

With pyridine; ammonium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1246/cl.1980.1373

Reference yield:

Acetic acid (2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6R)-3-acetoxy-6-allyloxy-5-amino-4-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-2-acetoxymethyl-5-amino-4-benzyloxy-tetrahydro-pyran-3-yl ester → [(4aR,6R,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy)-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester (76951-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / tetrahydrofuran

2: 75 percent / conc. aq. ammonia, ethanol (1:2) / 4.5 h / 50 °C

3: 88 percent / p-toluenesulfonic acid

With pyridine; ammonium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1246/cl.1980.1373

upstream raw materials:

C₃₈H₄₆N₂O₁₃

2,2-dimethoxy-propane

benzyl chloroformate

Downstream raw materials:

Tetradecanoic acid (2R,3S,4R,5R,6R)-6-allyloxy-2-((2R,3R,4R,5S,6R)-4-benzyloxy-3-benzyloxycarbonylamino-5-hydroxy-6-tetradecanoyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxycarbonylamino-4-tetradecanoyloxy-tetrahydro-pyran-3-yl ester

Tetradecanoic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-((2R,3R,4R,5S,6R)-4-benzyloxy-3-benzyloxycarbonylamino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-3-benzyloxycarbonylamino-5-tetradecanoyloxy-tetrahydro-pyran-4-yl ester