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

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-4-((2R,3R,4S,5S,6R)-4-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 389119-79-3
• Molecular Formula: C₅₄H₆₀O₁₃
• Molecular Weight: 917.063

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

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

Chemical Property:

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

There total 11 articles about Acetic acid (2R,3S,4S,5R,6R)-4-((2R,3R,4S,5S,6R)-4-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-allyloxy-3,5-bis-benzyloxy-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: 52.0%

2-propenyl 6-O-acetyl-2,4-di-O-benzyl-β-D-galactopyranoside (389119-59-9) + 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate (389119-61-3) → Acetic acid (2R,3S,4S,5R,6R)-4-((2R,3R,4S,5S,6R)-4-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (389119-79-3)

Guidance literature:

With 4 Angstroem MS; boron trifluoride diethyl etherate; In dichloromethane; at 24 ℃; for 18h;

DOI:10.1016/S0008-6215(01)00222-1

Reference yield:

allyl 4,6-O-benzylidene-β-D-galactopyranoside (71925-95-6) → Acetic acid (2R,3S,4S,5R,6R)-4-((2R,3R,4S,5S,6R)-4-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (389119-79-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 81 percent / Bu₃SnO; tetrabutylammonium iodide / Heating

2.1: 59 percent / 80 percent aq AcOH / 0.83 h / 86 °C

3.1: NaH (in oil) / 24 °C

4.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1 h / 24 °C

5.1: 1.04 g / Py

6.1: RhCl(PPh₃)3 / ethanol; toluene; H₂O / 20 h / Heating

6.2: 81 percent / 2N HCl / 1 h / Heating

7.1: 75 percent / 60 percent NaH / CH₂Cl₂ / 1 h / 22 °C

8.1: 52 percent / 10 percent BF₃-Et₂O; 4 Angstroem MS / CH₂Cl₂ / 18 h / 24 °C

With pyridine; RhCl(PPh₃)3; 4 Angstroem MS; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In ethanol; dichloromethane; water; toluene;

DOI:10.1016/S0008-6215(01)00222-1

Reference yield:

allyl β-D-galactopyranoside (2595-07-5,821794-45-0) → Acetic acid (2R,3S,4S,5R,6R)-4-((2R,3R,4S,5S,6R)-4-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (389119-79-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 70 percent / 0.5 h / 22 °C

2.1: 81 percent / Bu₃SnO; tetrabutylammonium iodide / Heating

3.1: 59 percent / 80 percent aq AcOH / 0.83 h / 86 °C

4.1: NaH (in oil) / 24 °C

5.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1 h / 24 °C

6.1: 1.04 g / Py

7.1: RhCl(PPh₃)3 / ethanol; toluene; H₂O / 20 h / Heating

7.2: 81 percent / 2N HCl / 1 h / Heating

8.1: 75 percent / 60 percent NaH / CH₂Cl₂ / 1 h / 22 °C

9.1: 52 percent / 10 percent BF₃-Et₂O; 4 Angstroem MS / CH₂Cl₂ / 18 h / 24 °C

With pyridine; RhCl(PPh₃)3; 4 Angstroem MS; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In ethanol; dichloromethane; water; toluene;

DOI:10.1016/S0008-6215(01)00222-1

upstream raw materials:

2-propenyl 6-O-acetyl-2,4-di-O-benzyl-β-D-galactopyranoside

3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

allyl 4,6-O-benzylidene-β-D-galactopyranoside

allyl β-D-galactopyranoside

Downstream raw materials:

2-propenyl 2,4-O-benzyl-3-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside

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