(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-6-methyl-oxepan-3-ol

Base Information

Chemical Name:(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-6-methyl-oxepan-3-ol
CAS No.:440635-14-3
Molecular Formula:C₂₃H₃₀O₅
Molecular Weight:386.488
Hs Code.:

Synonyms:(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-6-methyl-oxepan-3-ol

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Chemical Property of (2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-6-methyl-oxepan-3-ol

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Technology Process of (2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-6-methyl-oxepan-3-ol

There total 13 articles about (2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-6-methyl-oxepan-3-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: 89.0%

: 440635-13-2
(4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene

: 440635-14-3
(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-6-methyl-oxepan-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1016/S0040-4020(02)00038-8

Reference yield:

: 391235-78-2
(1S,6R,8S)-8-(benzyloxy)methyl-3,3-di-tert-butyl-2,4,7-trioxa-3-silabicyclo[4.4.0]deca-9-one

: 440635-14-3
(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-6-methyl-oxepan-3-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: H₂ / 20 percent Pd(OH)2/C / ethyl acetate / 1 h

2.1: 1.26 g / imidazole / dimethylformamide / 3 h / 20 °C

3.1: BF₃*OEt₂; molecular sieves 3 Angstroem / CH₂Cl₂; hexane / 0.33 h / -78 °C

3.2: 72 percent / PPTS / methanol / 4 h / 20 °C

4.1: 95 percent / tetrahydrofuran; toluene / 0.58 h / 0 °C

5.1: 87 percent / 1,1,1-trifluoroacetone; Oxone(R); further reagents / acetonitrile; acetone / 5 h / 0 °C

6.1: 98 percent / LiBHEt₃ / tetrahydrofuran / 0.5 h / 0 °C

7.1: 88 percent / aq. KOH / methanol / 2.5 h / 20 °C

8.1: 96 percent / KH / tetrahydrofuran / 1 h / 20 °C

9.1: 89 percent / Bu₄NF / tetrahydrofuran / 5 h / 20 °C

With 1H-imidazole; potassium hydroxide; oxone; 1,1,1-trifluoro-2-propanone; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; lithium triethylborohydride; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4020(02)00038-8

Reference yield:

: 391235-90-8
4-Benzyloxy-3-bromo-1-((4S,5R)-2,2-di-tert-butyl-5-hydroxy-[1,3,2]dioxasilinan-4-yl)-butan-2-one

: 440635-14-3
(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-6-methyl-oxepan-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 83 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

2.1: H₂ / 20 percent Pd(OH)2/C / ethyl acetate / 1 h

3.1: 1.26 g / imidazole / dimethylformamide / 3 h / 20 °C

4.1: BF₃*OEt₂; molecular sieves 3 Angstroem / CH₂Cl₂; hexane / 0.33 h / -78 °C

4.2: 72 percent / PPTS / methanol / 4 h / 20 °C

5.1: 95 percent / tetrahydrofuran; toluene / 0.58 h / 0 °C

6.1: 87 percent / 1,1,1-trifluoroacetone; Oxone(R); further reagents / acetonitrile; acetone / 5 h / 0 °C

7.1: 98 percent / LiBHEt₃ / tetrahydrofuran / 0.5 h / 0 °C

8.1: 88 percent / aq. KOH / methanol / 2.5 h / 20 °C

9.1: 96 percent / KH / tetrahydrofuran / 1 h / 20 °C

10.1: 89 percent / Bu₄NF / tetrahydrofuran / 5 h / 20 °C

With 1H-imidazole; potassium hydroxide; oxone; 1,1,1-trifluoro-2-propanone; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; lithium triethylborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4020(02)00038-8