N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-[(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]-tetrahydro-pyran-3-yl}-acetamide

Base Information

• Chemical Name: N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-[(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]-tetrahydro-pyran-3-yl}-acetamide
• CAS No.: 192065-37-5
• Molecular Formula: C₄₉H₆₁NO₁₁
• Molecular Weight: 840.023

Synonyms:N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-[(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]-tetrahydro-pyran-3-yl}-acetamide

Chemical Property of N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-[(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]-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,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-[(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]-tetrahydro-pyran-3-yl}-acetamide

There total 10 articles about N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-[(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]-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: 73.0%

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 (192065-23-9) → N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-[(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]-tetrahydro-pyran-3-yl}-acetamide (192065-37-5)

Guidance literature:

With methanol; camphor-10-sulfonic acid; In dichloromethane; for 16h;

DOI:10.1021/jo9621534

Reference yield:

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 (183805-71-2) → N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-[(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]-tetrahydro-pyran-3-yl}-acetamide (192065-37-5)

Guidance literature:

Multi-step reaction with 9 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

9: 73 percent / CSA, MeOH / CH₂Cl₂ / 16 h

With pyridine; methanol; sodium tetrahydroborate; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; ethanol; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; Dess-Martin periodane; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

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 → N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-[(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]-tetrahydro-pyran-3-yl}-acetamide (192065-37-5)

Guidance literature:

Multi-step reaction with 10 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

10: 73 percent / CSA, MeOH / CH₂Cl₂ / 16 h

With pyridine; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; ethanol; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; Dess-Martin periodane; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo9621534

upstream raw materials:

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

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

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

C₅₉H₈₁NO₁₁Si

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