6-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-methylene-D-xylo-hexitol

Base Information

Chemical Name:6-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-methylene-D-xylo-hexitol
CAS No.:260804-80-6
Molecular Formula:C₃₀H₄₄O₇Si
Molecular Weight:544.761
Hs Code.:

Synonyms:6-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-methylene-D-xylo-hexitol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 6-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-methylene-D-xylo-hexitol

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Technology Process of 6-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-methylene-D-xylo-hexitol

There total 5 articles about 6-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-methylene-D-xylo-hexitol 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: 96.0%

: 19493-09-5
Methylenetriphenylphosphorane

: 260804-79-3
D-threo-D-glycero-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-hexosulitol

: 260804-80-6
6-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-methylene-D-xylo-hexitol

Guidance literature:: In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/jo982448c

Reference yield:

: 69602-93-3
5,6-O-isopropylidene-L-galactonic acid γ-lactone

: 260804-80-6
6-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-methylene-D-xylo-hexitol

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / iPr₂NEt; Bu₄NI / 3 h / 70 °C

2: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

3: 99.7 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 1 h / 20 °C

4: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5: 96 percent / tetrahydrofuran / -78 - 20 °C

With dmap; lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Alkylation / 2: Reduction / 3: Substitution / 4: Oxidation / 5: Wittig reaction;
DOI:10.1021/jo982448c

Reference yield:

: 260804-76-0
5,6-O-isopropylidene-2,3-di-O-methoxymethyl-L-galactono-γ-lactone

: 260804-80-6
6-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-(methoxymethyl)-3-methylene-D-xylo-hexitol

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

2: 99.7 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 1 h / 20 °C

3: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4: 96 percent / tetrahydrofuran / -78 - 20 °C

With dmap; lithium aluminium tetrahydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: Substitution / 3: Oxidation / 4: Wittig reaction;
DOI:10.1021/jo982448c