1016985-81-1

Basic information

• Product Name: methyl (4R,5R)-5-benzyloxymethoxy-7-(4-methoxyphenylmethyloxy)-4-methyl-4-(triethylsiloxy)-2-heptynoate
• Synonyms: methyl (4R,5R)-5-benzyloxymethoxy-7-(4-methoxyphenylmethyloxy)-4-methyl-4-(triethylsiloxy)-2-heptynoate
• CAS NO: 1016985-81-1
• Molecular Weight: 556.772
• Mol File: 1016985-81-1.mol

Chemical Properties

• CAS DataBase Reference: methyl (4R,5R)-5-benzyloxymethoxy-7-(4-methoxyphenylmethyloxy)-4-methyl-4-(triethylsiloxy)-2-heptynoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (4R,5R)-5-benzyloxymethoxy-7-(4-methoxyphenylmethyloxy)-4-methyl-4-(triethylsiloxy)-2-heptynoate(1016985-81-1)
• EPA Substance Registry System: methyl (4R,5R)-5-benzyloxymethoxy-7-(4-methoxyphenylmethyloxy)-4-methyl-4-(triethylsiloxy)-2-heptynoate(1016985-81-1)

Safety Data

• Hazardous Substances Data: 1016985-81-1(Hazardous Substances Data)

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 1016985-80-0 methyl (4R,5R)-5-hydroxy-7-(4-methoxyphenylmethyloxy)-4-methyl-4-(triethylsiloxy)-2-heptynoate 

Downstream Products

• 1016985-82-2 (4R,5R)-5-benzyloxymethoxy-7-(4-methoxyphenylmethyloxy)-4-methyl-4-(triethylsiloxy)-2-heptynol 

Relevant articles and documents

Formal total synthesis of fostriecin via 1,4-asymmetric induction using cobalt-alkyne complex

(Chemical Equation Presented) The synthesis of a protected dephosphofostriecin, and thereby a formal synthesis of fostriecin, has been accomplished. Two of the four chiral centers are controlled by an external chiral auxiliary and the other two are synthesized stereoselectively, one by a novel 1,4-asymmetric induction using cobalt-alkyne complex, and the other by 1,3-asymmetric induction.

Formal total synthesis of fostriecin by 1,4-asymmetric induction with an alkyne-cobalt complex

The synthesis of a protected dephosphofostriecin, and thereby a formal synthesis of fostriecin, has been accomplished. The synthetic challenges were the construction of four stereogenic centers and the conformationally labile cis-cis-trans-triene moiety. Previous total syntheses have employed at least two asymmetric reactions that required the use of an external chiral auxiliary. Although remote stereoinduction in a 1,4-relationship is considered difficult, we have developed a notable 1,4-asymmetric induction that utilizes an alkyne-cobalt complex for the control of C5 stereochemistry by the C8 stereogenic center. The stereochemistry at C11 was established by 1,3-asymmetric induction with a higherorder alkynyl-zinc reagent. Thus, only one asymmetric reaction requiring an external chiral auxiliary was employed in this route. The labile cis-cis-transtriene unit was constructed at a late stage of the synthesis by diastereoselective coupling of a dienyne and an aldehyde unit, followed by reduction.