3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1,2-O-isopropylidene-sn-glycerol

Base Information

• Chemical Name: 3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1,2-O-isopropylidene-sn-glycerol
• CAS No.: 137895-66-0
• Molecular Formula: C₃₈H₄₈O₁₁S
• Molecular Weight: 712.859

Synonyms:3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1,2-O-isopropylidene-sn-glycerol

Chemical Property of 3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1,2-O-isopropylidene-sn-glycerol

Chemical Property:

Purity/Quality:

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Technology Process of 3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1,2-O-isopropylidene-sn-glycerol

There total 9 articles about 3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-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: 86.0%

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + 6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-β-D-glucopyranosyl fluoride (137895-65-9) → 3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1,2-O-isopropylidene-sn-glycerol (137895-66-0)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; 4 A molecular sieve; silver perchlorate; tin(ll) chloride; In diethyl ether; for 48h; Ambient temperature;

DOI:10.1021/ja00028a036

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → 3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1,2-O-isopropylidene-sn-glycerol (137895-66-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / NaH / dimethylformamide / 4 h / Ambient temperature

2: dimethyldioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

3: tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / Ambient temperature

4: 76 percent / 4-(dimethylamino)pyridine (DMAP), pyridine / 12 h / 35 °C

5: 99 percent / NaH / dimethylformamide / 3 h / Ambient temperature

6: 85 percent / ethanol / 3 h / Heating

7: 86 percent / SnCl₂, AgClO₄, 2,6-di-tert-butylpyridine, 4A molecular sieves / diethyl ether / 48 h / Ambient temperature

With pyridine; dmap; 2,6-di-tert-butyl-pyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; 3,3-dimethyldioxirane; sodium hydride; tin(ll) chloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja00028a036

Reference yield:

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (137915-37-8) → 3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1,2-O-isopropylidene-sn-glycerol (137895-66-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / NaH / dimethylformamide / 4 h / Ambient temperature

2: dimethyldioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

3: tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / Ambient temperature

4: 76 percent / 4-(dimethylamino)pyridine (DMAP), pyridine / 12 h / 35 °C

5: 99 percent / NaH / dimethylformamide / 3 h / Ambient temperature

6: 85 percent / ethanol / 3 h / Heating

7: 86 percent / SnCl₂, AgClO₄, 2,6-di-tert-butylpyridine, 4A molecular sieves / diethyl ether / 48 h / Ambient temperature

With pyridine; dmap; 2,6-di-tert-butyl-pyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; 3,3-dimethyldioxirane; sodium hydride; tin(ll) chloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja00028a036

upstream raw materials:

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-β-D-glucopyranosyl fluoride

p-Methoxybenzyl bromide

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

Downstream raw materials:

3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-sn-glycerol

3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1-O-linolenoyl-sn-glycerol

3-O-<6-deoxy-2,3,4-tri-O-(4-methoxybenzyl)-6-(thioacetyl)-α-D-glucopyranosyl>-1-O-linolenoyl-2-O-palmitoyl-sn-glycerol

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