phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-β-L-threo-pentopyranoside

Base Information

• Chemical Name: phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-β-L-threo-pentopyranoside
• CAS No.: 168567-19-9
• Molecular Formula: C₂₉H₃₁NO₄S
• Molecular Weight: 489.635
• Mol file: 168567-19-9.mol

Synonyms:phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-β-L-threo-pentopyranoside

Chemical Property of phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-β-L-threo-pentopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-β-L-threo-pentopyranoside

There total 1 articles about phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-β-L-threo-pentopyranoside 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: 48.0%

thiophenol (108-98-5) + methyl 2,4-dideoxy-4-amino>-3-O-methyl-α-L-threo-pentopyranoside (129834-77-1) → phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-α-L-threo-pentopyranoside (168567-18-8) + phenyl 2,4-dideoxy-4--3-O-methyl-1-thio-β-L-threo-pentopyranoside (168567-19-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 - 25 ℃; for 2h;

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--3-O-methyl-α-L-threo-pentopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-β-D-galactopyranoside (168567-29-1)

Guidance literature:

Multi-step reaction with 3 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

3: 99 percent / Ph₃SnH, AIBN / benzene / 0.33 h / Heating

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

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:

thiophenol

methyl 2,4-dideoxy-4-amino>-3-O-methyl-α-L-threo-pentopyranoside

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--2-iodo-3-O-methyl-α-L-lyxo-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