(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

Base Information

• Chemical Name: (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
• CAS No.: 168567-28-0
• Molecular Formula: C₄₅H₅₂INO₁₁
• Molecular Weight: 909.812

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 9 articles about (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 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:

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--2-iodo-3-O-methyl-α-L-lyxo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside (168567-28-0)

Guidance literature:

Multi-step reaction with 3 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

With Oxone; iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; boron trifluoride diethyl etherate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ja00126a013

Reference yield:

phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-α-L-threo-pentopyranoside (168567-18-8) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / oxone / methanol; tetrahydrofuran; H₂O / 0.33 h / 0 °C

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

With Oxone; iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; acetic acid; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja00126a013

Reference yield:

phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-β-L-threo-pentopyranoside (168567-19-9) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / oxone / methanol; tetrahydrofuran; H₂O / 0.33 h / 0 °C

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

With Oxone; iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; acetic acid; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja00126a013

upstream raw materials:

1,5-anhydro-2,4-dideoxy-4--3-O-methyl-L-threo-pent-1-enitol

(4-methoxyphenyl)methyl 6-deoxy-3-O-<(4-methoxyphenyl)methyl>-4-O-(trimethylsilyl)-β-D-galactopyranoside

p-Methoxybenzyl bromide

6-deoxy-D-glucal

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>-β-D-galactopyranoside

(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

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