N-[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 155501-09-0
• Molecular Formula: C₂₄H₂₉NO₆
• Molecular Weight: 427.497
• Mol file: 155501-09-0.mol

Synonyms:N-[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-acetamide

Chemical Property of N-[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-acetamide

There total 1 articles about N-[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-acetamide 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: 65.0%

p-methoxybenzyl chloride (824-94-2) + methyl 2-acetamido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside (155500-95-1) → N-[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-acetamide (155501-09-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(94)85080-1

Reference yield: 79.0%

N-[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-acetamide (155501-09-0) → N-[(1S,2R,3S,6S)-2-Benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-4-oxo-cyclohexyl]-acetamide (155501-10-3)

Guidance literature:

With sulfuric acid; mercury(II) sulfate; In 1,4-dioxane; water; at 80 ℃;

DOI:10.1016/0040-4039(94)85080-1

Reference yield:

N-[(2S,3R,4R,5S)-4-Benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-methylene-tetrahydro-pyran-3-yl]-acetamide (155501-09-0) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((1R,2R,3S,4S,6S)-3-acetylamino-2,4,6-trihydroxy-cyclohexyloxy)-tetrahydro-pyran-4-yl ester (848822-06-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 79 percent / HgSO₄, H₂SO₄ / dioxane; H₂O / 80 °C

2: 93 percent / NaBH₄ / acetic acid

3: 59 percent / NaH / dimethylformamide

4: 77 percent / DDQ / CH₂Cl₂; H₂O

5: 50 percent / TMSOTf, 4 Angstroem mol. sieves / CH₂Cl₂ / 0 °C

6: N₂H₄*H₂O / ethanol

7: pyridine

8: 76 percent / H₂ / Pd-C / methanol; acetic acid

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; hydrogen; sodium hydride; hydrazine hydrate; mercury(II) sulfate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(94)85080-1

upstream raw materials:

p-methoxybenzyl chloride

methyl 2-acetamido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

Downstream raw materials:

N-[(1S,2R,3S,6S)-2-Benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-4-oxo-cyclohexyl]-acetamide

N-[(1S,2R,3R,4S,6S)-2-Benzyloxy-4,6-dihydroxy-3-(4-methoxy-benzyloxy)-cyclohexyl]-acetamide

N-((1S,2R,3R,4S,6S)-2,4,6-Tris-benzyloxy-3-hydroxy-cyclohexyl)-acetamide

N-[(1S,2R,3R,4S,6S)-2,4,6-Tris-benzyloxy-3-(4-methoxy-benzyloxy)-cyclohexyl]-acetamide