Acetic acid (2R,3R,4S,5R)-6-acetoxy-4,5-bis-benzyloxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R)-6-acetoxy-4,5-bis-benzyloxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 80325-48-0
• Molecular Formula: C₅₈H₆₂O₁₃
• Molecular Weight: 967.122
• Mol file: 80325-48-0.mol

Synonyms:Acetic acid (2R,3R,4S,5R)-6-acetoxy-4,5-bis-benzyloxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2R,3R,4S,5R)-6-acetoxy-4,5-bis-benzyloxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R)-6-acetoxy-4,5-bis-benzyloxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about Acetic acid (2R,3R,4S,5R)-6-acetoxy-4,5-bis-benzyloxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl 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: 84.0%

acetic anhydride (108-24-7) + 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose (30608-09-4) → Acetic acid (2R,3R,4S,5R)-6-acetoxy-4,5-bis-benzyloxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (80325-48-0)

Guidance literature:

With trifluoroacetic acid; In acetic acid; for 2.5h; Ambient temperature;

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → Acetic acid (2R,3R,4S,5R)-6-acetoxy-4,5-bis-benzyloxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (80325-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1: BF₃*OEt₂ / CH₂Cl₂ / 2 h / -38 °C

2: 84 percent / CF₃COOH / acetic acid / 2.5 h / Ambient temperature

With boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane; acetic acid;

Reference yield:

1,6-Anhydro-2,3-di-O-benzyl-β-D-glucopyranose (80325-47-9) → Acetic acid (2R,3R,4S,5R)-6-acetoxy-4,5-bis-benzyloxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (80325-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1: BF₃*OEt₂ / CH₂Cl₂ / 2 h / -38 °C

2: 84 percent / CF₃COOH / acetic acid / 2.5 h / Ambient temperature

With boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane; acetic acid;

upstream raw materials:

acetic anhydride

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

1,6-Anhydro-2,3-di-O-benzyl-β-D-glucopyranose

Downstream raw materials:

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

[(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-((1R,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol

Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-((1R,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester