4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
CAS No.:335197-27-8
Molecular Formula:C₃₁H₃₂Cl₃NO₉
Molecular Weight:668.955
Hs Code.:

Synonyms:4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of 4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of 4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

There total 13 articles about 4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-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: 95.0%

: 545-06-2
trichloroacetonitrile

: 4-Methoxy-benzoic acid (3R,4S,5R)-2-bromo-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

: 335197-27-8
4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; for 12h;
DOI:10.1021/ja004098t

Reference yield:

: 545-06-2
trichloroacetonitrile

: 3,4-di-O-(4-methoxybenzyl)-2-O-(4-methoxybenzoyl)-α/β-D-xylopyranose

: 335197-27-8
4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; for 12h;
DOI:10.1021/ja012119t

Reference yield:

: 62446-93-9
1,2,3,4-tetra-O-acetyl-D-xylopyranose

: 335197-27-8
4-Methoxy-benzoic acid (3R,4S,5R)-4,5-bis-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / HBr; AcOH / CH₂Cl₂ / 4 h / 0 - 25 °C

2.1: 82 percent / 2,6-lutidine / nitromethane / 12 h / 25 °C

3.1: NaOMe / methanol / 3 h / 25 °C

4.1: NaH / tetrahydrofuran / 0 °C

4.2: 5.14 g / tetrabutylammonium chloride / tetrahydrofuran / 4 h / Heating

5.1: ZnCl₂ / CH₂Cl₂ / -60 - 0 °C

6.1: 3.4 g / NaOMe / methanol / 4 h / 25 °C

7.1: 97 percent / DMAP; Et₃N / CH₂Cl₂ / 48 h / 25 °C

8.1: 88 percent / NBS; H₂O / CH₂Cl₂ / 1 h / 25 °C

9.1: 555 mg / DBU / CH₂Cl₂ / 12 h / 25 °C

With 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; water; hydrogen bromide; sodium methylate; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; nitromethane; dichloromethane;
DOI:10.1021/ja012119t