Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester
CAS No.:245047-76-1
Molecular Formula:C₃₁H₄₂O₁₃S
Molecular Weight:654.733
Hs Code.:

Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester

Synonyms:Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester

There total 5 articles about Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester 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: 77.0%

: 98-59-9
p-toluenesulfonyl chloride

: 245047-75-0
Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-5-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-6-methoxy-tetrahydro-pyran-3-yl ester

: 245047-76-1
Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With dmap; In pyridine; at 0 - 4 ℃; for 36h;
DOI:10.3891/acta.chem.scand.53-0480

Reference yield:

: 20839-38-7,23392-30-5,23392-33-8,63864-93-7,65309-96-8,65309-99-1,67393-10-6,82264-32-2,23392-32-7
methyl 6-O-benzyl-α-D-glucopyranoside

: 245047-76-1
Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 15.5 h / 45 - 95 °C

2: 4-dimethylaminopyridine / pyridine / 20 °C

3: 90 percent / Bu₄NF*3H₂O / tetrahydrofuran / 3 h / 0 °C

4: 77 percent / 4-dimethylaminopyridine / pyridine / 36 h / 0 - 4 °C

With dmap; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; 1: Alkylation / 2: Acetylation / 3: Hydrolysis / 4: Esterification;
DOI:10.3891/acta.chem.scand.53-0480

Reference yield:

: 199484-66-7
toluene-4-sulfonic acid 2-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-ethoxy}-ethyl ester

: 245047-76-1
Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-benzyloxymethyl-6-methoxy-5-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 15.5 h / 45 - 95 °C

2: 4-dimethylaminopyridine / pyridine / 20 °C

3: 90 percent / Bu₄NF*3H₂O / tetrahydrofuran / 3 h / 0 °C

4: 77 percent / 4-dimethylaminopyridine / pyridine / 36 h / 0 - 4 °C

With dmap; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; 1: Alkylation / 2: Acetylation / 3: Hydrolysis / 4: Esterification;
DOI:10.3891/acta.chem.scand.53-0480