(2S,3S,4S,5R,6R)-2-((benzyloxy)carbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-2-((benzyloxy)carbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1045730-24-2
• Molecular Formula: C₂₁H₂₂Cl₃NO₁₀
• Molecular Weight: 554.765

Synonyms:(2S,3S,4S,5R,6R)-2-((benzyloxy)carbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2S,3S,4S,5R,6R)-2-((benzyloxy)carbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

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Technology Process of (2S,3S,4S,5R,6R)-2-((benzyloxy)carbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 2 articles about (2S,3S,4S,5R,6R)-2-((benzyloxy)carbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 85.0%

trichloroacetonitrile (545-06-2) + α,β-D-glucuronate → (2S,3S,4S,5R,6R)-2-((benzyloxy)carbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1045730-24-2)

Guidance literature:

With polymer-supported DBU; In dichloromethane; at 25 ℃; for 1h;

DOI:10.1016/j.bmc.2008.05.009

Reference yield: 85.0%

benzyl 2,3,4-tri-O-acetyl-D-glucopyranose uronate + trichloroacetonitrile (545-06-2) → (2S,3S,4S,5R,6R)-2-((benzyloxy)carbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1045730-24-2)

Guidance literature:

With polymer-supported 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃;

DOI:10.1002/chem.201002798

Reference yield: 88.0%

(2S,3S,4S,5R,6R)-2-((benzyloxy)carbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1045730-24-2) + (S)-2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-4-nitroisoindoline-1,3-dione (1384967-23-0) → (2S,3S,4S,5R,6S)-2-((benzyloxy)carbonyl)-6-(2-ethoxy-4-((S)-2-(methylsulfonyl)-1-(4-nitro-1,3-dioxoisoindolin-2-yl)ethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate (1384967-24-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -18 - 25 ℃; for 6h; Molecular sieve;

upstream raw materials:

trichloroacetonitrile

Downstream raw materials:

C₃₁H₃₄N₂O₁₅S

(S)-4-amino-2-[1-(3-ethoxy-4-glucopyranuroxy-phenyl)-2-methanefulfonyl-ethyl]-isoindole-1,3-dione

(2S,3S,4S,5R,6S)-2-((benzyloxy)carbonyl)-6-(2-ethoxy-4-((S)-2-(methylsulfonyl)-1-(4-nitro-1,3-dioxoisoindolin-2-yl)ethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate

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