4-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl ester

Base Information

• Chemical Name: 4-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl ester
• CAS No.: 161804-41-7
• Molecular Formula: C₄₀H₄₄O₁₁
• Molecular Weight: 700.783
• Mol file: 161804-41-7.mol

Synonyms:4-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl ester

Chemical Property of 4-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl ester

There total 3 articles about 4-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl 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: 11.0%

4-hydroxy-3,5-dimethoxybenzoic acid ethyl ester (3943-80-4) + 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (125164-10-5) → 4-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl ester + 4-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl ester (161804-41-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -15 - -10 ℃;

DOI:10.1080/00397919908086202

Reference yield:

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose (4356-77-8,35094-65-6,61277-56-3,65556-30-1,78185-13-4,78185-15-6,109958-31-8,109958-33-0,113532-02-8,59433-13-5) → 4-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl ester (161804-41-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / NH₃ / acetonitrile; methanol / 24 h / Ambient temperature

2: 80.5 percent / NaH

3: 60 percent / BF₃*Et₂O / CH₂Cl₂ / -15 - -10 °C

With boron trifluoride diethyl etherate; ammonia; sodium hydride; In methanol; dichloromethane; acetonitrile;

DOI:10.1080/00397919908086202

Reference yield:

6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose (88567-49-1,88567-50-4,93361-01-4,101802-94-2,101802-97-5,127875-38-1) → 4-((2S,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-benzoic acid ethyl ester (161804-41-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80.5 percent / NaH

2: 60 percent / BF₃*Et₂O / CH₂Cl₂ / -15 - -10 °C

With boron trifluoride diethyl etherate; sodium hydride; In dichloromethane;

DOI:10.1080/00397919908086202

upstream raw materials:

4-hydroxy-3,5-dimethoxybenzoic acid ethyl ester

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

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

Downstream raw materials:

3,5-Dimethoxy-4-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid