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

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Chemical Name:4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-[(2S,3R,4R,5S)-3-acetoxy-2-(2,2,2-trichloro-acetimidoyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester
CAS No.:335197-11-0
Molecular Formula:C₄₄H₅₆Cl₃NO₁₄Si
Molecular Weight:957.371
Hs Code.:

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

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

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

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

There total 24 articles about 4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-[(2S,3R,4R,5S)-3-acetoxy-2-(2,2,2-trichloro-acetimidoyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-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: 88.0%

: 545-06-2
trichloroacetonitrile

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

: 335197-11-0
4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-[(2S,3R,4R,5S)-3-acetoxy-2-(2,2,2-trichloro-acetimidoyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-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:

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

: 335197-11-0
4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-[(2S,3R,4R,5S)-3-acetoxy-2-(2,2,2-trichloro-acetimidoyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 11 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

10.1: 93 percent / BF₃*Et₂O; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - -20 °C

11.1: NBS; H₂O / CH₂Cl₂ / 2 h / 25 °C

11.2: 98 percent / DBU / CH₂Cl₂ / 12 h / 25 °C

With 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; 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

Reference yield:

: 1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,142130-89-0,123163-97-3
1,2,3,4-tetra-O-acetyl-L-arabinopyranose

: 335197-11-0
4-Methoxy-benzoic acid (2S,3R,4S,5R)-2-[(2S,3R,4R,5S)-3-acetoxy-2-(2,2,2-trichloro-acetimidoyloxy)-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 80 percent / SnCl₄ / CH₂Cl₂ / 6 h / -78 °C

2.1: 95 percent / NaOMe / methanol / 6 h / 25 °C

3.1: CSA / CH₂Cl₂ / 12 h / 25 °C

4.1: DMAP; Et₃N / CH₂Cl₂ / 2 h / 25 °C

5.1: 5.1 g / Amberlite IR-118H / methanol / 12 h / 25 °C

6.1: 90 percent / lutidine / CH₂Cl₂ / 2 h / -70 - -60 °C

7.1: 93 percent / BF₃*Et₂O; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - -20 °C

8.1: NBS; H₂O / CH₂Cl₂ / 2 h / 25 °C

8.2: 98 percent / DBU / CH₂Cl₂ / 12 h / 25 °C

With dmap; N-Bromosuccinimide; 4 A molecular sieve; Amberlite IR-118H; lutidine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; water; sodium methylate; tin(IV) chloride; triethylamine; In methanol; dichloromethane;
DOI:10.1021/ja012119t