(2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate

Base Information

• Chemical Name: (2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate
• CAS No.: 123493-06-1
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.346
• Mol file: 123493-06-1.mol

Synonyms:(2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate

Chemical Property of (2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate

There total 13 articles about (2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate 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: 71.0%

methanol (67-56-1) + (1S,2S,4R,6S)-7-benzoyl-4-methoxy-2-methyl-3-oxa-7-azabicyclo(4.2.0)octan-8-one (115133-12-5) → (2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate (123493-06-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; for 32h; Heating;

DOI:10.1016/0040-4020(89)80126-7

Reference yield:

(1S,2S,4R,6S)-4-methoxy-7-(4-methoxyphenyl)-2-methyl-3-oxa-7-azabicyclo(4.2.0)octan-8-one (115133-11-4) → (2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate (123493-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / ceric ammonium nitrate / acetonitrile; H₂O

2: 98 percent / Et₃N, 4-DMAP / CH₂Cl₂

3: 71 percent / 1,8-diazabicyclo<5.4.0>undecane / Heating

With dmap; ammonium cerium(IV) nitrate; triethylamine; 1,8-diazabicyclo-[5,4,0]-undecane; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)96544-4

Reference yield:

(1S,2S,4R,6S)-4-methoxy-2-methyl-3-oxa-7-azabicyclo(4.2.0)octan-8-one (115184-80-0) → (2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate (123493-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Et₃N, 4-DMAP / CH₂Cl₂

2: 71 percent / 1,8-diazabicyclo<5.4.0>undecane / Heating

With dmap; triethylamine; 1,8-diazabicyclo-[5,4,0]-undecane; In dichloromethane;

DOI:10.1016/S0040-4039(00)96544-4

upstream raw materials:

methanol

(1S,2S,4R,6S)-7-benzoyl-4-methoxy-2-methyl-3-oxa-7-azabicyclo(4.2.0)octan-8-one

(1S,2S,4R,6S)-4-methoxy-2-methyl-3-oxa-7-azabicyclo(4.2.0)octan-8-one

(1S,2S,4R,5R)-4-hydroxy-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo(3.2.0)heptan-7-one

Downstream raw materials:

methyl 3-benzamido-2,3,6-trideoxy-α-L-arabino-hexopyranoside

(2S,3R,4S,6R)-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2-pyran-3-carboxylic acid