N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3S,4S)-4-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-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,3S,4S)-4-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide
CAS No.:192065-23-9
Molecular Formula:C₅₂H₆₅NO₁₁
Molecular Weight:880.088
Hs Code.:

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

There total 9 articles about N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3S,4S)-4-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-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: 76.0%

: 192065-22-8
C₅₉H₈₃NO₁₄SSi

: 192065-23-9
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3S,4S)-4-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; for 2h;
DOI:10.1021/jo9621534

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

: 192065-23-9
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3S,4S)-4-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: Multi-step reaction with 9 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: Dess-Martin periodinane / CH₂Cl₂ / 1 h

6: 15.0 mg / LiBH₄ / tetrahydrofuran / 0 °C

7: 1) O₃, 2) NaBH₄ / 1) MeOH, -78 deg C, 20 s, 2) MeOH, -78 deg C -> room temperature, 15 min

8: 77 percent / Et₃N / CH₂Cl₂ / 0.5 h

9: 76 percent / TBAF / diethyl ether; tetrahydrofuran / 2 h

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; ethanol; tetrabutyl ammonium fluoride; dihydrogen peroxide; Dess-Martin periodane; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo9621534

Reference yield:

: 183805-71-2
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-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

: 192065-23-9
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3S,4S)-4-hydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: Multi-step reaction with 8 steps

1: 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

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

3: tetrahydrofuran / 0.5 h / -78 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 1 h

5: 15.0 mg / LiBH₄ / tetrahydrofuran / 0 °C

6: 1) O₃, 2) NaBH₄ / 1) MeOH, -78 deg C, 20 s, 2) MeOH, -78 deg C -> room temperature, 15 min

7: 77 percent / Et₃N / CH₂Cl₂ / 0.5 h

8: 76 percent / TBAF / diethyl ether; tetrahydrofuran / 2 h

With pyridine; sodium tetrahydroborate; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; ethanol; tetrabutyl ammonium fluoride; dihydrogen peroxide; Dess-Martin periodane; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo9621534