(2-Bromo-ethyl)-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: (2-Bromo-ethyl)-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 127924-72-5
• Molecular Formula: C₃₃H₃₉BrNO₈P
• Molecular Weight: 688.552

Synonyms:(2-Bromo-ethyl)-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of (2-Bromo-ethyl)-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of (2-Bromo-ethyl)-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

There total 2 articles about (2-Bromo-ethyl)-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 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: 75.0%

(2-Bromo-ethyl)-phosphonic acid benzotriazol-1-yl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (127924-71-4) + 3-Hydroxypropionitrile (109-78-4) → (2-Bromo-ethyl)-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (127924-72-5)

Guidance literature:

at 20 ℃; for 4h;

DOI:10.1016/S0040-4039(01)80597-9

Reference yield:

methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside (40653-32-5,641635-63-4) → (2-Bromo-ethyl)-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (127924-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.17 h

2: 75 percent / 4 h / 20 °C

DOI:10.1016/S0040-4039(01)80597-9

Reference yield: 85.0%

(2-Bromo-ethyl)-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (127924-72-5) → Vinyl-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (127924-73-6)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1016/S0040-4039(01)80597-9

upstream raw materials:

(2-Bromo-ethyl)-phosphonic acid benzotriazol-1-yl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

3-Hydroxypropionitrile

methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

Vinyl-phosphonic acid 2-cyano-ethyl ester (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

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