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

Base Information

Chemical Name: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
CAS No.:183805-74-5
Molecular Formula:C₅₆H₇₅NO₁₁Si
Molecular Weight:966.297
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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: 97.0%

: 183805-75-6
N-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(2R,3S)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-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

: 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

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; for 2h;
DOI:10.1021/jo9621534

Reference yield:

: 183805-45-0
N-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-2,2-dimethyl-8-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / CrCl₂, NiCl₂ / tetrahydrofuran; dimethylformamide / 72 h

2: 2,6-lutidene

3: 1.) 9-BBN, H₂O₂, 2.) Dess-Martin periodinane / 1.) THF, 0 deg C, 2.) CH₂Cl₂

With 2,6-dimethylpyridine; chromium dichloride; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; Dess-Martin periodane; nickel dichloride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja960741t

Reference yield:

: 183805-39-2
(2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / CrCl₂, NiCl₂ / tetrahydrofuran; dimethylformamide / 72 h

2: 2,6-lutidene

3: 1.) 9-BBN, H₂O₂, 2.) Dess-Martin periodinane / 1.) THF, 0 deg C, 2.) CH₂Cl₂

With 2,6-dimethylpyridine; chromium dichloride; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; Dess-Martin periodane; nickel dichloride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja960741t