methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
• CAS No.: 144985-15-9
• Molecular Formula: C₁₉H₂₄O₆S
• Molecular Weight: 380.462
• Mol file: 144985-15-9.mol

Synonyms:methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Chemical Property of methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

There total 5 articles about methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-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 3-O-allyl-1-thio-β-D-galactopyranoside (144985-17-1) → methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (144985-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1: TsOH*H₂O / tetrahydrofuran

With toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)61200-5

Reference yield:

methyl 1-thio-β-D-galactopyranoside (155-30-6) → methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (144985-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Bu₂SnO, 2) Bu₄NBr / 1) toluene, THF, reflux, 2) THF, reflux

2: TsOH*H₂O / tetrahydrofuran

With tetrabutylammomium bromide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)61200-5

Reference yield:

methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (55722-48-0) → methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (144985-15-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOMe / methanol; tetrahydrofuran

2: 1) Bu₂SnO, 2) Bu₄NBr / 1) toluene, THF, reflux, 2) THF, reflux

3: TsOH*H₂O / tetrahydrofuran

With tetrabutylammomium bromide; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)61200-5

upstream raw materials:

acetic anhydride

(2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-methylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Methyl 3-O-allyl-1-thio-β-D-galactopyranoside

methyl 1-thio-β-D-galactopyranoside

Downstream raw materials:

(4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester

N-benzyloxycarbonyl-O-{O-(2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)}-L-serine benzyl ester

Acetic acid (2S,4aR,6S,7R,8S,8aS)-8-allyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester