1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol

Base Information

Chemical Name:1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol
CAS No.:884507-72-6
Molecular Formula:C₄₅H₄₇NO₆
Molecular Weight:697.871
Hs Code.:

Synonyms:1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol

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Chemical Property of 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol

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Technology Process of 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol

There total 3 articles about 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol 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: 55.0%

: 884507-71-5
1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-4-O-methanesulfonyl-D-glucitol

: 884507-72-6
1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jo8001134

Reference yield:

: 1021325-68-7
N-benzyloxycarbonyl 2,3,5,6-tetra-O-benzyl-α,β-D-glucofuranosylamine

: 884507-72-6
1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / Me₃SiOTf / acetonitrile / 82 h / -40 °C

2: 62 percent / Et₃N / CH₂Cl₂ / 5 h / 20 °C

3: t-BuOK / tetrahydrofuran / 12 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ol053078z

Reference yield:

: 884507-68-0
1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-D-glucitol

: 884507-72-6
1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol

Guidance literature:: Multi-step reaction with 2 steps

1: trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

2: 0.86 g / EDC; HOBt; Et₃N / dimethylformamide / 20 °C

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0529750