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

Base Information

• Chemical Name: 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
• CAS No.: 183805-71-2
• Molecular Formula: C₅₆H₇₅NO₁₀Si
• Molecular Weight: 950.298

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 3 articles about 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 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:

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 (183805-45-0) → 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)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 2,6-lutidene

With 2,6-dimethylpyridine; chromium dichloride; nickel dichloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja960741t

Reference yield:

(2S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2-(2-bromo-allyl)-6-methyl-tetrahydro-pyran (183805-39-2) → 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 (183805-71-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 2,6-lutidene

With 2,6-dimethylpyridine; chromium dichloride; nickel dichloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja960741t

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + 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-{(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-{(4aR,6S,7R,8R,8aS)-6-Benzyloxy-8-[(S)-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 (183905-38-6)

Guidance literature:

With 2,6-dimethylpyridine; Yield given. Yields of byproduct given;

DOI:10.1021/ja960741t

upstream raw materials:

t-butyldimethylsiyl triflate

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

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

Downstream raw materials:

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

C₅₉H₈₃NO₁₄SSi

C₅₈H₈₁NO₁₂Si

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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