ethyl (methyl 2,3-O-isopropylidene-6,7-dideoxy-4-phenylthionocarbonate-α-D-mannooctopyranosid)uronate

Base Information

Chemical Name:ethyl (methyl 2,3-O-isopropylidene-6,7-dideoxy-4-phenylthionocarbonate-α-D-mannooctopyranosid)uronate
CAS No.:740840-78-2
Molecular Formula:C₂₁H₂₈O₈S
Molecular Weight:440.515
Hs Code.:

Synonyms:ethyl (methyl 2,3-O-isopropylidene-6,7-dideoxy-4-phenylthionocarbonate-α-D-mannooctopyranosid)uronate

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Chemical Property of ethyl (methyl 2,3-O-isopropylidene-6,7-dideoxy-4-phenylthionocarbonate-α-D-mannooctopyranosid)uronate

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Technology Process of ethyl (methyl 2,3-O-isopropylidene-6,7-dideoxy-4-phenylthionocarbonate-α-D-mannooctopyranosid)uronate

There total 6 articles about ethyl (methyl 2,3-O-isopropylidene-6,7-dideoxy-4-phenylthionocarbonate-α-D-mannooctopyranosid)uronate 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: 82.0%

: 1005-56-7
phenylcarbonochloridothioate

: 740840-77-1
ethyl (methyl 4-O-benzyl-2,3-O-isopropylidene-6,7-dideoxy-α-D-manno-octopyranosid)uronate

: 740840-78-2
ethyl (methyl 2,3-O-isopropylidene-6,7-dideoxy-4-phenylthionocarbonate-α-D-mannooctopyranosid)uronate

Guidance literature:: With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; In toluene; at 20 ℃; for 4h;
DOI:10.1002/anie.200353478

Reference yield:

: 82185-79-3
methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside

: 740840-78-2
ethyl (methyl 2,3-O-isopropylidene-6,7-dideoxy-4-phenylthionocarbonate-α-D-mannooctopyranosid)uronate

Guidance literature:: Multi-step reaction with 4 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 23 °C

2: 503 mg / CH₂Cl₂ / 5 h / 23 °C

3: 88 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 3361.46 Torr

4: 82 percent / NHS; pyridine / toluene / 4 h / 20 °C

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; toluene; 1: Swern oxidation / 2: Wittig reaction;
DOI:10.1002/anie.200353478

Reference yield:

: 132032-75-8
methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

: 740840-78-2
ethyl (methyl 2,3-O-isopropylidene-6,7-dideoxy-4-phenylthionocarbonate-α-D-mannooctopyranosid)uronate

Guidance literature:: Multi-step reaction with 3 steps

1: 503 mg / CH₂Cl₂ / 5 h / 23 °C

2: 88 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 3361.46 Torr

3: 82 percent / NHS; pyridine / toluene / 4 h / 20 °C

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; palladium on activated charcoal; In ethanol; dichloromethane; toluene; 1: Wittig reaction;
DOI:10.1002/anie.200353478