(3R,5S,7R,8R,9S,10R)-10-Benzyloxy-7-benzyloxymethyl-3,8,9-trihydroxy-1,6-dioxaspiro[4.5]decane 3,8,9-tris(di-O-benzyl)phosphate

Base Information

Chemical Name:(3R,5S,7R,8R,9S,10R)-10-Benzyloxy-7-benzyloxymethyl-3,8,9-trihydroxy-1,6-dioxaspiro[4.5]decane 3,8,9-tris(di-O-benzyl)phosphate
CAS No.:302332-13-4
Molecular Formula:C₆₅H₆₇O₁₆P₃
Molecular Weight:1197.16
Hs Code.:

Synonyms:(3R,5S,7R,8R,9S,10R)-10-Benzyloxy-7-benzyloxymethyl-3,8,9-trihydroxy-1,6-dioxaspiro[4.5]decane 3,8,9-tris(di-O-benzyl)phosphate

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Chemical Property of (3R,5S,7R,8R,9S,10R)-10-Benzyloxy-7-benzyloxymethyl-3,8,9-trihydroxy-1,6-dioxaspiro[4.5]decane 3,8,9-tris(di-O-benzyl)phosphate

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Technology Process of (3R,5S,7R,8R,9S,10R)-10-Benzyloxy-7-benzyloxymethyl-3,8,9-trihydroxy-1,6-dioxaspiro[4.5]decane 3,8,9-tris(di-O-benzyl)phosphate

There total 8 articles about (3R,5S,7R,8R,9S,10R)-10-Benzyloxy-7-benzyloxymethyl-3,8,9-trihydroxy-1,6-dioxaspiro[4.5]decane 3,8,9-tris(di-O-benzyl)phosphate 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:

: Phosphorous acid dibenzyl ester (3R,5S,7R,8R,9R,10R)-10-benzyloxy-7-benzyloxymethyl-3,9-bis-(bis-benzyloxy-phosphanyloxy)-1,6-dioxa-spiro[4.5]dec-8-yl ester

: 302332-13-4
(3R,5S,7R,8R,9S,10R)-10-Benzyloxy-7-benzyloxymethyl-3,8,9-trihydroxy-1,6-dioxaspiro[4.5]decane 3,8,9-tris(di-O-benzyl)phosphate

Guidance literature:: With tert.-butylhydroperoxide; In 1,2-dichloro-ethane; acetonitrile; at 0 ℃; for 0.5h;
DOI:10.1002/1521-3765(20000804)6:15<2696::AID-CHEM2696>3.0.CO;2-Y

Reference yield:

: 108549-23-1
Dibenzyl N,N-diisopropylphosphoramidite

: 302332-13-4
(3R,5S,7R,8R,9S,10R)-10-Benzyloxy-7-benzyloxymethyl-3,8,9-trihydroxy-1,6-dioxaspiro[4.5]decane 3,8,9-tris(di-O-benzyl)phosphate

Guidance literature:: Multi-step reaction with 2 steps

1: 1H-tetrazole / 1,2-dichloro-ethane; acetonitrile / 0.5 h

2: 0.15 g / tert-BuOOH / 1,2-dichloro-ethane; acetonitrile / 0.5 h / 0 °C

With 1H-tetrazole; tert.-butylhydroperoxide; In 1,2-dichloro-ethane; acetonitrile; 1: Substitution / 2: Oxidation;
DOI:10.1002/1521-3765(20000804)6:15<2696::AID-CHEM2696>3.0.CO;2-Y

Reference yield:

: 197644-80-7
(2'S,3'S)-ethyl 2,6-di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside

: 302332-13-4
(3R,5S,7R,8R,9S,10R)-10-Benzyloxy-7-benzyloxymethyl-3,8,9-trihydroxy-1,6-dioxaspiro[4.5]decane 3,8,9-tris(di-O-benzyl)phosphate

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / H₂O; N-iodosuccinimide; TfOH / CH₂Cl₂; tetrahydrofuran / 2 h

2: 100 percent / DMSO; Ac₂O / 2 h / 70 °C

3: 86 percent / tetrahydrofuran / 0.5 h / -78 °C

4: 100 percent / H₂O; K₂OsO₄*2H₂O; NMO / acetone / 1 h

5: aq. AcOH / 2 h / Heating

6: 1H-tetrazole / 1,2-dichloro-ethane; acetonitrile / 0.5 h

7: 0.15 g / tert-BuOOH / 1,2-dichloro-ethane; acetonitrile / 0.5 h / 0 °C

With 1H-tetrazole; tert.-butylhydroperoxide; potassium osmate(VI); N-iodo-succinimide; N-methyl-2-indolinone; trifluorormethanesulfonic acid; water; acetic anhydride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetone; acetonitrile; 1: Hydrolysis / 2: Oxidation / 3: Addition / 4: Addition / 5: Cyclization / 6: Substitution / 7: Oxidation;
DOI:10.1002/1521-3765(20000804)6:15<2696::AID-CHEM2696>3.0.CO;2-Y