N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Base Information

Chemical Name:N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide
CAS No.:192065-33-1
Molecular Formula:C₅₃H₆₇NO₁₂
Molecular Weight:910.114
Hs Code.:

N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Synonyms:N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

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Chemical Property of N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

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Technology Process of N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

There total 7 articles about N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 63.0%

: 183805-85-8
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3S,4R)-2,4-dihydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-hept-6-enyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

: 192065-33-1
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1021/ja960741t

Reference yield:

: N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[2-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-but-3-enyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

: 192065-33-1
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 107.0 mg / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2: 1) 9-BBN, 2) 30percent H₂O₂, EtOH, phosphate buffer / 1) THF, hexanes, 0 deg C, 0.5 h; room temperature, 1 h, 2) THF, hexanes, room temperature, 2 h

3: 97 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 2 h

4: tetrahydrofuran / 0.5 h / -78 °C

5: 97 percent / TBAF / diethyl ether / 1 h

6: 63 percent / MCPBA, NaH₂PO₄ / CH₂Cl₂ / 24 h

With pyridine; 2,6-dimethylpyridine; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; ethanol; tetrabutyl ammonium fluoride; dihydrogen peroxide; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo9621534

Reference yield:

: 183805-74-5
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-formyl-4-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-butyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

: 192065-33-1
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3R,4R)-2,4-dihydroxy-5-oxiranyl-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-pentyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: tetrahydrofuran / 0.5 h / -78 °C

2: 97 percent / TBAF / diethyl ether / 1 h

3: 63 percent / MCPBA, NaH₂PO₄ / CH₂Cl₂ / 24 h

With sodium dihydrogenphosphate; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo9621534