(4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside

Base Information

• Chemical Name: (4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside
• CAS No.: 168567-29-1
• Molecular Formula: C₄₅H₅₃NO₁₁
• Molecular Weight: 783.916
• Mol file: 168567-29-1.mol

Synonyms:(4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside

Chemical Property of (4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside

There total 11 articles about (4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-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: 99.0%

(4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--2-iodo-3-O-methyl-α-L-lyxo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside (168567-28-0) → (4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside (168567-29-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); triphenylstannane; In benzene; for 0.333333h; Heating;

DOI:10.1021/ja00126a013

Reference yield:

methyl 2,4-dideoxy-4-amino>-3-O-methyl-α-L-threo-pentopyranoside (129834-77-1) → (4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside (168567-29-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 47 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -20 - 25 °C

2: 82 percent / oxone / methanol; tetrahydrofuran; H₂O / 0.33 h / 0 °C

3: 1.) I(sym-collidine)ClO₄, mol. sieves 4A, 2.) aq. AcOH / 1.) CH₂Cl₂, RT, 2 h, 2.) THF, RT, 30 min

4: 99 percent / Ph₃SnH, AIBN / benzene / 0.33 h / Heating

With Oxone; 2,2'-azobis(isobutyronitrile); iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; boron trifluoride diethyl etherate; triphenylstannane; acetic acid; In tetrahydrofuran; methanol; dichloromethane; water; benzene;

DOI:10.1021/ja00126a013

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside (168567-29-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 1 h, 2.) DMF, 80 deg C, 3 h

2: 1.) dimethyldioxirane / 1.) CH₂Cl₂, acetone, 0 deg C, 30 min, 2.) CH₂Cl₂, acetone, RT, 12 h

3: 1.) pyridine, 2.) K₂CO₃ / 1.) CH₂Cl₂, RT, 15 min, 2.) MeOH, RT, 90 min

4: 1.) I(sym-collidine)ClO₄, mol. sieves 4A, 2.) aq. AcOH / 1.) CH₂Cl₂, RT, 2 h, 2.) THF, RT, 30 min

5: 99 percent / Ph₃SnH, AIBN / benzene / 0.33 h / Heating

With pyridine; 2,2'-azobis(isobutyronitrile); iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; triphenylstannane; 3,3-dimethyldioxirane; di(n-butyl)tin oxide; potassium carbonate; acetic acid; cesium fluoride; In benzene;

DOI:10.1021/ja00126a013

upstream raw materials:

(4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--2-iodo-3-O-methyl-α-L-lyxo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside

p-Methoxybenzyl bromide

6-deoxy-D-glucal

1,5-anhydro-2,6-dideoxy-3-O-<(4-methoxyphenyl)methyl>-D-lyxo-hex-1-enopyranoside

Downstream raw materials:

(4-methoxyphenyl)methyl 6-deoxy-2-O-<2,4-dideoxy-4--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-4-O-(trifluoromethanesulfonyl)-β-D-galactopyranoside