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

Base Information

• Chemical Name: 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-4-O-methanesulfonyl-D-glucitol
• CAS No.: 884507-71-5
• Molecular Formula: C₄₆H₅₁NO₉S
• Molecular Weight: 793.978

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

Chemical Property of 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-4-O-methanesulfonyl-D-glucitol

Chemical Property:

Purity/Quality:

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Technology Process of 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-4-O-methanesulfonyl-D-glucitol

There total 2 articles about 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-4-O-methanesulfonyl-D-glucitol 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: 62.0%

1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-D-glucitol (884507-68-0) + methanesulfonyl chloride (124-63-0) → 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-4-O-methanesulfonyl-D-glucitol (884507-71-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/ol053078z

Reference yield:

N-benzyloxycarbonyl 2,3,5,6-tetra-O-benzyl-α,β-D-glucofuranosylamine (1021325-68-7) → 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-4-O-methanesulfonyl-D-glucitol (884507-71-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/ol053078z

Reference yield: 55.0%

1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-4-O-methanesulfonyl-D-glucitol (884507-71-5) → 1(R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-galactitol (884507-72-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo8001134

upstream raw materials:

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

methanesulfonyl chloride

N-benzyloxycarbonyl 2,3,5,6-tetra-O-benzyl-α,β-D-glucofuranosylamine

Downstream raw materials:

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

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

(1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol

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