benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside

Base Information

Chemical Name:benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside
CAS No.:412922-95-3
Molecular Formula:C₆₄H₉₅O₉P
Molecular Weight:1039.43
Hs Code.:

Synonyms:benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside

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Chemical Property of benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside

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Technology Process of benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside

There total 23 articles about benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside 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: 49.0%

: 314740-77-7
2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl triflate

: tetrabutylammonium benzyl 4,8,12,16,20-pentamethylpentacosylphosphate

: 412922-95-3
benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside

Guidance literature:: In toluene; at -78 ℃; for 6h;
DOI:10.1021/ja0123958

Reference yield:

: 37905-02-5
(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

: 412922-95-3
benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside

Guidance literature:: Multi-step reaction with 16 steps

1.1: KHMDS / toluene; tetrahydrofuran / 0.83 h / -78 - 20 °C

1.2: 76 percent / tetrahydrofuran; toluene / -78 - 20 °C

2.1: 96 percent / Na; MeOH / 2 h

3.1: 98 percent / H₂; NaHCO₃ / PtO₂ / tetrahydrofuran / 20 h / 2585.81 Torr

4.1: 93 percent / Ph₃P; DIAD / tetrahydrofuran / 0.08 h

5.1: 98 percent / MCPBA / CH₂Cl₂ / 0 - 20 °C

6.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.2: 90 percent / tetrahydrofuran / -78 - 20 °C

7.1: Na; MeOH / 2 h

8.1: 97 percent / H₂; NaHCO₃ / PtO₂ / tetrahydrofuran / 2585.81 Torr

9.1: 92 percent / Ph₃P; DIAD / tetrahydrofuran

10.1: 91 percent / MCPBA / CH₂Cl₂ / 0 - 20 °C

11.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

11.2: 90 percent / tetrahydrofuran / -78 - 20 °C

12.1: H₂ / Pd/C / atmospheric pressure

13.1: tetrazole / acetonitrile

14.1: tert-butyl hydroperoxide / acetonitrile; decane

15.1: 100 percent / CH₂Cl₂; H₂O / 1 h

16.1: 49 percent / toluene / 6 h / -78 °C

With 1H-tetrazole; methanol; tert.-butylhydroperoxide; di-isopropyl azodicarboxylate; hydrogen; sodium; potassium hexamethylsilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; decane; dichloromethane; water; toluene; acetonitrile; 1.1: Wittig olefination / 1.2: Wittig olefination / 4.1: Mitsunobu reaction / 9.1: Mitsunobu reaction;
DOI:10.1021/ja0123958

Reference yield:

: 73746-79-9,80698-15-3,107242-87-5,10603-03-9,823-22-3
α-methyl-δ-valerolactone

: 412922-95-3
benzyl 4,8,12,16,20-pentamethylpentacosylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-mannopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1.1: trimethylaluminium / CH₂Cl₂; heptane / -10 - 20 °C

1.2: 98 percent / CH₂Cl₂; heptane / 0 - 20 °C

2.1: 96 percent / NaH / tetrahydrofuran

3.1: 92 percent / DIBAL / tetrahydrofuran; toluene / 2 h / -78 °C

4.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 90 percent / tetrahydrofuran / -78 - 20 °C

5.1: H₂ / Pd/C / atmospheric pressure

6.1: tetrazole / acetonitrile

7.1: tert-butyl hydroperoxide / acetonitrile; decane

8.1: 100 percent / CH₂Cl₂; H₂O / 1 h

9.1: 49 percent / toluene / 6 h / -78 °C

With 1H-tetrazole; tert.-butylhydroperoxide; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; decane; n-heptane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/ja0123958