(2S,3S,8R,9S,10R)-9,10-Bis-allyloxy-2-allyloxymethyl-8-benzyloxy-3-benzyloxymethyl-1,4,6-trioxa-spiro[4.5]decane

Base Information

Chemical Name:(2S,3S,8R,9S,10R)-9,10-Bis-allyloxy-2-allyloxymethyl-8-benzyloxy-3-benzyloxymethyl-1,4,6-trioxa-spiro[4.5]decane
CAS No.:306725-94-0
Molecular Formula:C₃₂H₄₀O₈
Molecular Weight:552.665
Hs Code.:

Synonyms:(2S,3S,8R,9S,10R)-9,10-Bis-allyloxy-2-allyloxymethyl-8-benzyloxy-3-benzyloxymethyl-1,4,6-trioxa-spiro[4.5]decane

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Chemical Property of (2S,3S,8R,9S,10R)-9,10-Bis-allyloxy-2-allyloxymethyl-8-benzyloxy-3-benzyloxymethyl-1,4,6-trioxa-spiro[4.5]decane

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Technology Process of (2S,3S,8R,9S,10R)-9,10-Bis-allyloxy-2-allyloxymethyl-8-benzyloxy-3-benzyloxymethyl-1,4,6-trioxa-spiro[4.5]decane

There total 5 articles about (2S,3S,8R,9S,10R)-9,10-Bis-allyloxy-2-allyloxymethyl-8-benzyloxy-3-benzyloxymethyl-1,4,6-trioxa-spiro[4.5]decane 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: 97.0%

: 306725-81-5
(3R,4S,5R)-3,4-Bis-allyloxy-5-benzyloxy-tetrahydro-pyran-2-one

: 306725-82-6
((2S,3S)-4-Allyloxy-2,3-bis-trimethylsilanyloxy-butoxymethyl)-benzene

: 306725-94-0
(2S,3S,8R,9S,10R)-9,10-Bis-allyloxy-2-allyloxymethyl-8-benzyloxy-3-benzyloxymethyl-1,4,6-trioxa-spiro[4.5]decane

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 25 ℃; for 12h;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 78469-77-9,81076-11-1,128820-40-6,78513-03-8
(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

: 306725-94-0
(2S,3S,8R,9S,10R)-9,10-Bis-allyloxy-2-allyloxymethyl-8-benzyloxy-3-benzyloxymethyl-1,4,6-trioxa-spiro[4.5]decane

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 0.25 h / 0 °C

1.2: dimethylformamide / 2 h / 0 - 25 °C

2.1: 4.90 g / aq. HCl / methanol

3.1: HMDS / acetonitrile / 0.42 h

4.1: 97 percent / TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Metallation / 1.2: Etherification / 2.1: Hydrolysis / 3.1: Etherification / 4.1: Glycosidation;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 100-39-0
benzyl bromide

: 306725-94-0
(2S,3S,8R,9S,10R)-9,10-Bis-allyloxy-2-allyloxymethyl-8-benzyloxy-3-benzyloxymethyl-1,4,6-trioxa-spiro[4.5]decane

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.25 h / 0 °C

1.2: 92 percent / dimethylformamide / 2 h / 0 - 25 °C

2.1: NaH / dimethylformamide / 0.25 h / 0 °C

2.2: dimethylformamide / 2 h / 0 - 25 °C

3.1: 4.90 g / aq. HCl / methanol

4.1: HMDS / acetonitrile / 0.42 h

5.1: 97 percent / TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Metallation / 1.2: Etherification / 2.1: Metallation / 2.2: Etherification / 3.1: Hydrolysis / 4.1: Etherification / 5.1: Glycosidation;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8