methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate

Base Information

Chemical Name:methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate
CAS No.:288852-13-1
Molecular Formula:C₂₂H₂₃NO₈
Molecular Weight:429.427
Hs Code.:

Synonyms:methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate

Suppliers and Price of methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate

There total 8 articles about methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate 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: 84.0%

: 288852-12-0
methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate

: 288852-13-1
methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate

Guidance literature:: methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate; With ozone; at -78 ℃; for 0.25h;

With dimethylsulfide; at 20 ℃; Further stages.;
DOI:10.1021/ol990320r

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 288852-13-1
methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 81 percent / TMSOTf / CH₂Cl₂ / 1.25 h / -78 °C

2.1: 88 percent / LiBH₄ / methanol; diethyl ether / 0.25 h / Heating

3.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

4.1: 37 percent / indium / tetrahydrofuran; H₂O / 4.5 h

5.1: 64 percent / di-tert-butyl azodicarboxylate; Ph₃P / tetrahydrofuran / 20 °C

6.1: 88 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / H₂O; CH₂Cl₂ / 1.5 h

7.1: O₃ / 0.25 h / -78 °C

7.2: 84 percent / Me₂S / 20 °C

With indium; lithium borohydride; trimethylsilyl trifluoromethanesulfonate; di-tert-butyl-diazodicarboxylate; Dess-Martin periodane; ozone; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1.1: Alkylation / 2.1: Reduction / 3.1: Oxidation / 4.1: Condensation / 5.1: Mitsunobu reaction / 6.1: ether cleavage / 7.1: ozonolysis / 7.2: Reduction;
DOI:10.1021/ol990320r

Reference yield:

: (S)-2-(N-benzyloxycarbonyl)amino-3-(4-methoxyphenyl)methoxypropanal

: 288852-13-1
methyl 4-O-benzoyl-3,5-dideoxy-5-(N-phenylmethoxycarbonyl)amino-α-L-threo-2-hexulopyranosonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 37 percent / indium / tetrahydrofuran; H₂O / 4.5 h

2.1: 64 percent / di-tert-butyl azodicarboxylate; Ph₃P / tetrahydrofuran / 20 °C

3.1: 88 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / H₂O; CH₂Cl₂ / 1.5 h

4.1: O₃ / 0.25 h / -78 °C

4.2: 84 percent / Me₂S / 20 °C

With indium; di-tert-butyl-diazodicarboxylate; ozone; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; 1.1: Condensation / 2.1: Mitsunobu reaction / 3.1: ether cleavage / 4.1: ozonolysis / 4.2: Reduction;
DOI:10.1021/ol990320r