methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside

Base Information

Chemical Name:methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside
CAS No.:651302-49-7
Molecular Formula:C₁₄H₁₅N₃O₄
Molecular Weight:289.291
Hs Code.:

Synonyms:methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside

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

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Chemical Property of methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside

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Technology Process of methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside

There total 4 articles about methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside 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: 42.0%

: 431935-41-0
methyl 2-O-benzoyl-3,4-dideoxy-6-O-tosyl-α-D-threo-hex-3-enopyranoside

: 651302-49-7
methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 75 - 80 ℃; for 2h;
DOI:10.1081/CAR-120026469

Reference yield:

: 3366-47-0
2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose

: 651302-49-7
methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 43 percent / BF₃*Et₂O / toluene; methanol / 0.42 h

2: 61 percent / LiAlH₄ / tetrahydrofuran / 0.58 h / 0 °C

3: 73 percent / Et₃N / CH₂Cl₂ / 48 h / 0 - 20 °C

4: PPh₃; DEAD / tetrahydrofuran / 0 °C

5: 42 percent / NaN₃ / dimethylformamide / 2 h / 75 - 80 °C

With lithium aluminium tetrahydride; sodium azide; boron trifluoride diethyl etherate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Mitsunobu reaction;
DOI:10.1081/CAR-120026469

Reference yield:

: 651302-31-7
methyl 2,4,6-tri-O-acetyl-3-deoxy-D-erythro-hex-2-enopyranoside

: 651302-49-7
methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 61 percent / LiAlH₄ / tetrahydrofuran / 0.58 h / 0 °C

2: 73 percent / Et₃N / CH₂Cl₂ / 48 h / 0 - 20 °C

3: PPh₃; DEAD / tetrahydrofuran / 0 °C

4: 42 percent / NaN₃ / dimethylformamide / 2 h / 75 - 80 °C

With lithium aluminium tetrahydride; sodium azide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Mitsunobu reaction;
DOI:10.1081/CAR-120026469