(1S,3R,4R,6S,8S,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane

Base Information

• Chemical Name: (1S,3R,4R,6S,8S,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane
• CAS No.: 848821-37-4
• Molecular Formula: C₂₈H₃₈I₂O₄Si
• Molecular Weight: 720.502

Synonyms:(1S,3R,4R,6S,8S,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane

Chemical Property of (1S,3R,4R,6S,8S,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane

Chemical Property:

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• Pictogram(s):  
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Technology Process of (1S,3R,4R,6S,8S,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane

There total 2 articles about (1S,3R,4R,6S,8S,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane 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:

(4R,5R)-2-[1-allyl-1-tert-butyldimethylsilyloxy-3-butenyl]-4,5-diphenyl-1,3-dioxolane (848821-31-8) → (1S,3R,4R,6S,8S,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane (848821-37-4)

Guidance literature:

With N-iodo-succinimide; water; In acetonitrile; at -40 - 0 ℃; for 3h;

DOI:10.1002/anie.200461584

Reference yield:

(4R,5R)-2-[1-allyl-1-tert-butyldimethylsilyloxy-3-butenyl]-4,5-diphenyl-1,3-dioxolane (848821-31-8) → (1S,3R,4R,6S,8S,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane (848821-37-4) + 6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane

Guidance literature:

With N-iodo-succinimide; water; In acetonitrile; at -40 - 0 ℃; for 3h;

DOI:10.1016/j.tet.2008.02.088

Reference yield: 73.0%

(1S,3R,4R,6S,8S,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane (848821-37-4) → (1R,2R)-2-[(2S,3S,5R)-3-allyl-3-tert-butyldimethylsilyloxy-5-iodomethyl-2-tetrahydrofuranyloxy]-1,2-diphenylethanol (1030605-20-9)

Guidance literature:

With zinc trifluoromethanesulfonate; zinc; In tetrahydrofuran; at 70 ℃; for 5h;

DOI:10.1016/j.tet.2008.02.088

upstream raw materials:

(4R,5R)-2-[1-allyl-1-tert-butyldimethylsilyloxy-3-butenyl]-4,5-diphenyl-1,3-dioxolane

Downstream raw materials:

(1R,2R)-2-[(2S,3S,5R)-3-allyl-3-tert-butyldimethylsilyloxy-5-iodomethyl-2-tetrahydrofuranyloxy]-1,2-diphenylethanol

(1S,3R,4R,6R,8S,10R)-6-[2,2-bis(methoxycarbonyl)ethyl]-10-iodomethyl-3,4-diphenyl-8-tert-butyldimethylsilyloxy-2,5,11-trioxabicyclo[6.3.0]undecane

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