(2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside

Base Information

• Chemical Name: (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside
• CAS No.: 1402142-33-9
• Molecular Formula: C₄₀H₄₂O₈
• Molecular Weight: 650.769
• Mol file: 1402142-33-9.mol

Synonyms:

Chemical Property of (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside

There total 8 articles about (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 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: 19.0%

danishefsky's diene (54125-02-9) + 2-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyloxy)acetaldehyde (1402142-45-3) → (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (1402142-33-9) + (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (1402142-32-8)

Guidance literature:

danishefsky's diene; 2-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyloxy)acetaldehyde; With chromium chloride; C₂₇H₃₁NO₂; In diethyl ether; at -20 ℃; for 43.5h; Inert atmosphere; Molecular sieve;

With trifluoroacetic acid; In diethyl ether; at -20 ℃; for 3h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/ejoc.201200277

Reference yield:

D-Galactose (10257-28-0) → (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (1402142-33-9) + (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (1402142-32-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium acetate / 2.25 h / 100 °C / air

2.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Molecular sieve; Inert atmosphere

3.1: sodium acetate / methanol / 3 h / 20 °C / Inert atmosphere

3.2: DOWEX-50 ion exchange resin / 17 h / 20 °C / Inert atmosphere

4.1: sodium hydride / mineral oil / 1.5 h / 115 - 130 °C / Inert atmosphere

4.2: DOWEX-50 ion exchange resin / 17 h / 20 °C / Inert atmosphere

5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 20 °C / Inert atmosphere

6.1: sodium periodate / tetrahydrofuran / 0 °C / pH 7 / Inert atmosphere; aq. buffer

7.1: titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol / toluene / 2.5 h / 0 °C / Inert atmosphere

7.2: Inert atmosphere

With titanium(IV) isopropylate; sodium periodate; osmium(VIII) oxide; boron trifluoride diethyl etherate; (R)-1,1'-Bi-2-naphthol; sodium acetate; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; mineral oil; tert-butyl alcohol; 7.1: hetero-Diels-Alder;

DOI:10.1002/ejoc.201200277

Reference yield:

1,2,3,4,6-penta-O-acetyl-β-D-galactopyranoside (7226-48-4,10357-30-9,14199-54-3,14199-55-4,14199-57-6,18968-06-4,32445-64-0,32475-75-5,52645-74-6,67322-02-5,100018-31-3,101540-16-3,140148-47-6) → (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (1402142-33-9) + (2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (1402142-32-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Molecular sieve; Inert atmosphere

2.1: sodium acetate / methanol / 3 h / 20 °C / Inert atmosphere

2.2: DOWEX-50 ion exchange resin / 17 h / 20 °C / Inert atmosphere

3.1: sodium hydride / mineral oil / 1.5 h / 115 - 130 °C / Inert atmosphere

3.2: DOWEX-50 ion exchange resin / 17 h / 20 °C / Inert atmosphere

4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 20 °C / Inert atmosphere

5.1: sodium periodate / tetrahydrofuran / 0 °C / pH 7 / Inert atmosphere; aq. buffer

6.1: titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol / toluene / 2.5 h / 0 °C / Inert atmosphere

6.2: Inert atmosphere

With titanium(IV) isopropylate; sodium periodate; osmium(VIII) oxide; boron trifluoride diethyl etherate; (R)-1,1'-Bi-2-naphthol; sodium acetate; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; mineral oil; tert-butyl alcohol; 6.1: hetero-Diels-Alder;

DOI:10.1002/ejoc.201200277

upstream raw materials:

D-Galactose

1,2,3,4,6-penta-O-acetyl-β-D-galactopyranoside

danishefsky's diene

2-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyloxy)acetaldehyde