(2S,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3,4-diol
• CAS No.: 847237-47-2
• Molecular Formula: C₂₁H₃₀O₁₁
• Molecular Weight: 458.463

Synonyms:

Chemical Property of (2S,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3,4-diol

There total 4 articles about (2S,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3,4-diol 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',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-60-8,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4) → (2S,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3,4-diol (847237-47-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / molecular sieves 4 Angstroem; boron trifluoride etherate / CH₂Cl₂

2: 9.8 g / NaOMe / methanol / 20 °C

3: 3.0 g / H₂SO₄ / dimethylformamide; acetone / 1 h / Heating

With 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.carres.2004.11.017

Reference yield:

phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside (34361-44-9) → (2S,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3,4-diol (847237-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 9.8 g / NaOMe / methanol / 20 °C

2: 3.0 g / H₂SO₄ / dimethylformamide; acetone / 1 h / Heating

With sulfuric acid; sodium methylate; In methanol; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.carres.2004.11.017

Reference yield:

phenol (108-95-2,27073-41-2) → (2S,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3,4-diol (847237-47-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / molecular sieves 4 Angstroem; boron trifluoride etherate / CH₂Cl₂

2: 9.8 g / NaOMe / methanol / 20 °C

3: 3.0 g / H₂SO₄ / dimethylformamide; acetone / 1 h / Heating

With 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.carres.2004.11.017

upstream raw materials:

2,2-dimethoxy-propane

phenyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose

phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside

Downstream raw materials:

phenyl 2,3,6-tri-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside

C₅₃H₄₆O₁₅

phenyl 2,3,6-tri-O-benzoyl-4-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside

C₆₀H₅₀O₁₆

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