(2R,4aR,6S,7R,8S,8aR)-6-((E)-(2S,3S,4R)-2-Amino-3,4-bis-benzyloxy-octadec-6-enyloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Base Information

Chemical Name:(2R,4aR,6S,7R,8S,8aR)-6-((E)-(2S,3S,4R)-2-Amino-3,4-bis-benzyloxy-octadec-6-enyloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
CAS No.:930283-68-4
Molecular Formula:C₅₂H₆₉NO₈
Molecular Weight:836.122
Hs Code.:

Synonyms:(2R,4aR,6S,7R,8S,8aR)-6-((E)-(2S,3S,4R)-2-Amino-3,4-bis-benzyloxy-octadec-6-enyloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Chemical Property of (2R,4aR,6S,7R,8S,8aR)-6-((E)-(2S,3S,4R)-2-Amino-3,4-bis-benzyloxy-octadec-6-enyloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Technology Process of (2R,4aR,6S,7R,8S,8aR)-6-((E)-(2S,3S,4R)-2-Amino-3,4-bis-benzyloxy-octadec-6-enyloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

There total 7 articles about (2R,4aR,6S,7R,8S,8aR)-6-((E)-(2S,3S,4R)-2-Amino-3,4-bis-benzyloxy-octadec-6-enyloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 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:

: 2-azido-3,4-di-O-benzyl-1-O-(2-O-benzyl-4,6-O-benzylidene-3-O-levulinyl-α-D-galactopyranosyl)-D-ribo-octadeca-6-ene-1-ol

: 930283-68-4
(2R,4aR,6S,7R,8S,8aR)-6-((E)-(2S,3S,4R)-2-Amino-3,4-bis-benzyloxy-octadec-6-enyloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: C₅₇H₇₅NO₁₀

Guidance literature:: 2-azido-3,4-di-O-benzyl-1-O-(2-O-benzyl-4,6-O-benzylidene-3-O-levulinyl-α-D-galactopyranosyl)-D-ribo-octadeca-6-ene-1-ol; With trimethylphosphane; In tetrahydrofuran; toluene; at 0 - 20 ℃;

With sodium hydroxide; In tetrahydrofuran; water; toluene;

Reference yield:

: (2R,4aR,7R,8S,8aR)-7-Benzyloxy-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 930283-68-4
(2R,4aR,6S,7R,8S,8aR)-6-((E)-(2S,3S,4R)-2-Amino-3,4-bis-benzyloxy-octadec-6-enyloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / EDC; DMAP / CH₂Cl₂

2: 91 percent / NBS / acetone / 0.17 h

3: 77 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

4: 46 percent / TMSOTf; molecular sieves AW-300 / tetrahydrofuran / 2.5 h / 0 °C

5: tetrahydrofuran; toluene / 20 °C

6: aq. NaOH / 5 h

With dmap; sodium hydroxide; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; acetone; toluene; 5: Staudinger reaction;
DOI:10.1016/j.bmc.2005.02.018

Reference yield:

: 2-O-benzyl-4,6-O-benzylidene-3-O-levulinoyl-D-galactopyranoside

: 930283-68-4
(2R,4aR,6S,7R,8S,8aR)-6-((E)-(2S,3S,4R)-2-Amino-3,4-bis-benzyloxy-octadec-6-enyloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

2: 46 percent / TMSOTf; molecular sieves AW-300 / tetrahydrofuran / 2.5 h / 0 °C

3: tetrahydrofuran; toluene / 20 °C

4: aq. NaOH / 5 h

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; toluene; 3: Staudinger reaction;
DOI:10.1016/j.bmc.2005.02.018