Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester
• CAS No.: 194800-99-2
• Molecular Formula: C₃₄H₄₅IO₇SSi
• Molecular Weight: 752.783
• Mol file: 194800-99-2.mol

Synonyms:Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester

Chemical Property of Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester

There total 7 articles about Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester 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: 83.0%

methanesulfonyl chloride (124-63-0) + (1R,2R,3S,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexanol (194800-90-3) → Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester (194800-99-2)

Guidance literature:

With triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(97)01325-7

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester (194800-99-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

2: 99 percent / LiAlH(OtBu)3 / tetrahydrofuran / Ambient temperature

3: 83 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(97)01325-7

Reference yield:

2-iodobenzyliodide (4622-38-2) → Methanesulfonic acid (1R,2S,3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexyl ester (194800-99-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / NaH / dimethylformamide / Ambient temperature

2: Hg(OCOCF₃)2 / acetone; H₂O / Ambient temperature

3: 86 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

4: 99 percent / LiAlH(OtBu)3 / tetrahydrofuran / Ambient temperature

5: 83 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; mercury(II) trifluoroacetate; sodium hydride; lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(97)01325-7

upstream raw materials:

methanesulfonyl chloride

(1R,2R,3S,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexanol

t-butyldimethylsiyl triflate

2-iodobenzyliodide

Downstream raw materials:

(4R,5S,6R)-5,6-Bis-benzyloxy-4-(2-iodo-benzyloxy)-cyclohex-2-enone

Methanesulfonic acid (1R,2S,3R,4S,5S)-3,4-bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexyl ester