82188-56-5

Upstream product

• 13322-79-7 (2R,3S,4R,6S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 66409-28-7 (1R,2R,4S,6R)-4-Methoxy-2-methyl-3,7-dioxa-bicyclo[4.1.0]heptane 
• 72075-75-3 (2R,3R,4R,6S)-4-Azido-6-methoxy-2-methyl-tetrahydro-pyran-3-ol 
• 72075-74-2 methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

Synthesis of thienamycin from D-glucose

Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): STR1 wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R1 is lower alkyl or aralkyl, such as benzyl and the like; and R2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.

3-Amino-4-C-carboxy-2,3,4,6-tetradeoxy-D-arabino-hexose trimethylene dithioacetal

Disclosed is a chiral, total synthesis of thienamycin from D-glucose, which proceeds via intermediates I, II, and III and joins aldehyde IV or acid V, which are known to be useful in the total synthesis of thienamycin (VI): STR1 wherein R1 is hydrogen or a removable protecting group; R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms.

Methyl 3-azido-4-C-cyano-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside

Disclosed is methyl 3-azido-4-C-cyano-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside and processes for its preparation from methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside via the 4-bromo-4-deoxy intermediate; wherein the two inversions of configuration at C-4 result in a net retention of the α-D-arabino stereochemistry.