[(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

Base Information

• Chemical Name: [(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
• CAS No.: 80339-87-3
• Molecular Formula: C₇₄H₇₈O₁₅
• Molecular Weight: 1207.42
• Mol file: 80339-87-3.mol

Synonyms:

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 5 articles about [(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 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:

1,6-Anhydro-2,3-di-O-benzyl-β-D-glucopyranose (80325-47-9) → [(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 (80339-87-3)

Guidance literature:

Multi-step reaction with 6 steps

1: BF₃*OEt₂ / CH₂Cl₂ / 2 h / -38 °C

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

3: 90 percent / C₆H₅CH₂NH₂ / diethyl ether / 1.5 h / Ambient temperature

4: NaH / CH₂Cl₂ / 3 h / Ambient temperature

5: 57 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -40 °C

6: 96 percent / NaOMe / methanol; diethyl ether / 5 h / Ambient temperature

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; benzylamine; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; acetic acid;

Reference yield:

Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-6-hydroxy-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 (80339-87-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / CH₂Cl₂ / 3 h / Ambient temperature

2: 57 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -40 °C

3: 96 percent / NaOMe / methanol; diethyl ether / 5 h / Ambient temperature

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In methanol; diethyl ether; dichloromethane;

Reference yield:

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) → [(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 (80339-87-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / C₆H₅CH₂NH₂ / diethyl ether / 1.5 h / Ambient temperature

2: NaH / CH₂Cl₂ / 3 h / Ambient temperature

3: 57 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -40 °C

4: 96 percent / NaOMe / methanol; diethyl ether / 5 h / Ambient temperature

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; benzylamine; In methanol; diethyl ether; dichloromethane;

upstream raw materials:

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

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

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

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