3-O-(2,3,4-tri-O-benzyl-6-O-p-methoxyphenyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol

Base Information

Chemical Name:3-O-(2,3,4-tri-O-benzyl-6-O-p-methoxyphenyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol
CAS No.:887700-85-8
Molecular Formula:C₄₀H₄₆O₉
Molecular Weight:670.8
Hs Code.:

Synonyms:3-O-(2,3,4-tri-O-benzyl-6-O-p-methoxyphenyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol

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Chemical Property of 3-O-(2,3,4-tri-O-benzyl-6-O-p-methoxyphenyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol

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Technology Process of 3-O-(2,3,4-tri-O-benzyl-6-O-p-methoxyphenyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol

There total 5 articles about 3-O-(2,3,4-tri-O-benzyl-6-O-p-methoxyphenyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol 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:

: (2R,3R,4S,5R,6R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3,4,5-triol

: 100-44-7
benzyl chloride

: 887700-85-8
3-O-(2,3,4-tri-O-benzyl-6-O-p-methoxyphenyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol

Guidance literature:: With potassium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 16h;
DOI:10.1016/j.carres.2006.01.021

Reference yield:

: Acetic acid (2R,3S,4S,5R)-4,5-diacetoxy-6-hydroxy-2-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yl ester

: 887700-85-8
3-O-(2,3,4-tri-O-benzyl-6-O-p-methoxyphenyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol

Guidance literature:: Multi-step reaction with 4 steps

1: 0.790 g / DBU / CH₂Cl₂ / 4 h / 20 °C

2: 72 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 5 h / -20 °C

3: MeONa / methanol

4: 0.450 g / KOH / dimethylsulfoxide / 16 h / 20 °C

With potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; dimethyl sulfoxide; 3: Zemplen O-deacetylation;
DOI:10.1016/j.carres.2006.01.021

Reference yield:

: 1,2,3,4-tetra-O-acetyl-6-O-p-methoxyphenyl-D-galactopyranose

: 887700-85-8
3-O-(2,3,4-tri-O-benzyl-6-O-p-methoxyphenyl-β-D-galactopyranosyl)-1,2-O-isopropylidene-sn-glycerol

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / hydrazine acetate / dimethylformamide / 1 h / 50 °C

2: 0.790 g / DBU / CH₂Cl₂ / 4 h / 20 °C

3: 72 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 5 h / -20 °C

4: MeONa / methanol

5: 0.450 g / KOH / dimethylsulfoxide / 16 h / 20 °C

With potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4: Zemplen O-deacetylation;
DOI:10.1016/j.carres.2006.01.021