(1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-4-ene

Base Information

• Chemical Name: (1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-4-ene
• CAS No.: 144152-54-5
• Molecular Formula: C₂₄H₃₃Cl₃INO₆Si
• Molecular Weight: 692.878

Synonyms:

Chemical Property of (1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-4-ene

There total 15 articles about (1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-4-ene 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%

(1R,2S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-eth-(E)-ylidene]-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]octan-2-ol (149883-63-6) + trichloroacetonitrile (545-06-2) → (1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.02,6]undec-4-ene (144152-54-5,144178-98-3)

Guidance literature:

With iodonium(di-γ-collidine) perchlorate; 1,8-diazabicyclo[5.4.0]undec-7-ene;

Reference yield:

2,2,2-Trichloro-acetimidic acid (1R,2S,4S,5R)-3-[2-(tert-butyl-dimethyl-silanyloxy)-eth-(Z)-ylidene]-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester → (1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.02,6]undec-4-ene (144152-54-5,144178-98-3)

Guidance literature:

With iodonium(di-γ-collidine) perchlorate; In acetonitrile; at 55 ℃; for 1h;

DOI:10.1021/ja00068a025

Reference yield:

(-)-1,6-anhydro-4-O-benzoyl-β-D-mannopyranose (7225-53-8) → (1R,2S,6R,7S,8R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-ethyl]-7-(4-methoxy-benzyloxy)-4-trichloromethyl-3,9,11-trioxa-5-aza-tricyclo[6.2.1.02,6]undec-4-ene (144152-54-5,144178-98-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Bu₂SnO, 2.) n-Bu₄NI / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, reflux, 40 h

2: 98 percent / Dess-Martin periodinane, t-BuOH / CH₂Cl₂ / 2 h

3: 1.) NaH / 1.) THF, 0 deg C, 1 h, 2.) THF, -78 deg C, 1 h

4: 92 percent / L-selectride / tetrahydrofuran / 2 h

5: 68 percent / imidazole / dimethylformamide / 4 h

6: 70 percent / DBU

7: I(Coll)ClO₄ / acetonitrile / 1 h / 55 °C

With 1H-imidazole; iodonium(di-γ-collidine) perchlorate; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00068a025

upstream raw materials:

(1R,2S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-eth-(E)-ylidene]-4-(4-methoxy-benzyloxy)-6,8-dioxa-bicyclo[3.2.1]octan-2-ol

trichloroacetonitrile

(-)-1,6-anhydro-4-O-benzoyl-2,3-isopropylidene-β-D-mannopyranose

(-)-1,6-anhydro-4-O-benzoyl-β-D-mannopyranose

Downstream raw materials:

2'-methyl-(1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-3-C-vinyl-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

2'-methyl-(1,6-anhydro-3-deoxy-3-C-formyl-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

2'-methyl-(3-C-acetyl-1,6-anhydro-3-deoxy-2-O-(p-methoxybenzyl)-β-D-altropyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

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