(2R,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propa-1,2-dienyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propa-1,2-dienyl-tetrahydro-pyran
CAS No.:142888-01-5
Molecular Formula:C₃₀H₃₁N₃O₄
Molecular Weight:497.594
Hs Code.:

Synonyms:(2R,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propa-1,2-dienyl-tetrahydro-pyran

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Chemical Property of (2R,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propa-1,2-dienyl-tetrahydro-pyran

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Technology Process of (2R,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propa-1,2-dienyl-tetrahydro-pyran

There total 3 articles about (2R,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propa-1,2-dienyl-tetrahydro-pyran 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: 65.0%

: 13361-64-3
trimethyl(propargyl)silane

: 94715-75-0
2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl nitrate

: 142888-01-5
(2R,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propa-1,2-dienyl-tetrahydro-pyran

Guidance literature:: With boron trifluoride diethyl etherate; In acetonitrile; for 10h; 0 deg C to RT;
DOI:10.1016/S0040-4039(00)79826-1

Reference yield:

: 80040-79-5
3,4,6-tri-O-benzyl-D-galactal

: 142888-01-5
(2R,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propa-1,2-dienyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: NaN₃, cerium ammonium nitrate (CAN) / acetonitrile / 2.5 h

2: 65 percent / BF₃OEt₂ / acetonitrile / 10 h / 0 deg C to RT

With sodium azide; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; In acetonitrile;
DOI:10.1016/S0040-4039(00)79826-1

Reference yield:

: 94715-75-0
2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl nitrate

: 142888-01-5
(2R,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propa-1,2-dienyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: acetic acid / 8 h / 100 °C

2: BF₃OEt₂ / 1) 0 deg C to RT, 12 h, 2) RT, 12 h

With boron trifluoride diethyl etherate; In acetic acid;
DOI:10.1016/S0040-4039(00)79826-1