(1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane

Base Information

Chemical Name:(1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane
CAS No.:144067-00-5
Molecular Formula:C₃₆H₅₈O₅Si₂
Molecular Weight:627.025
Hs Code.:

(1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane

Synonyms:(1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane

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Chemical Property of (1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane

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Technology Process of (1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane

There total 12 articles about (1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane 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: 95.0%

: 144066-99-9
Methanesulfonic acid (1S,2R,3R,4S,6R)-1-benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-methyl-cyclohexylmethyl ester

: 144067-00-5
(1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane

Guidance literature:: With sodium hydride; In diethyl ether; at 45 ℃; for 12h;
DOI:10.1039/c39920001118

Reference yield:

: 496-64-0
3-hydroxy-2-pyrone

: 144067-00-5
(1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) PhB(OH)2, 2.) 2,2-dimethylpropane-1,3-diol / 1.) benzene, 90 deg C, 48 h, 2.) benzene, 25 deg C, 30 min

2: 80 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.5 h / 0 - 25 °C

3: 90 percent / Red-Al / hexane; tetrahydrofuran / 1 h / Heating

4: 100 percent / camphorsulfonic acid (CSA) / CH₂Cl₂

5: 1.) BH₃*THF, 2.) H₂O₂, NaOH / 1.) CH₂Cl₂, 25 deg C, 1 h, 2.) CH₂Cl₂, 25 deg C, 30 min

6: 90 percent / DMAP / CH₂Cl₂ / 0.33 h / 25 °C

7: 100 percent / camphorsulfonic acid (CSA) / methanol

8: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

9: 95 percent / MeONa / methanol / 2 h / 25 °C

10: 80 percent / DMAP / CH₂Cl₂ / 2 h / 0 °C

11: 95 percent / NaH / diethyl ether / 12 h / 45 °C

With 2,6-dimethylpyridine; dmap; sodium hydroxide; borane-THF; camphor-10-sulfonic acid; dihydrogen peroxide; sodium methylate; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; 2,2-Dimethyl-1,3-propanediol; sodium bis(2-methoxyethoxy)aluminium dihydride; phenylboronic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1039/c39920001118

Reference yield:

: 100-39-0
benzyl bromide

: 144067-00-5
(1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane

Guidance literature:: Multi-step reaction with 10 steps

1: 80 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.5 h / 0 - 25 °C

2: 90 percent / Red-Al / hexane; tetrahydrofuran / 1 h / Heating

3: 100 percent / camphorsulfonic acid (CSA) / CH₂Cl₂

4: 1.) BH₃*THF, 2.) H₂O₂, NaOH / 1.) CH₂Cl₂, 25 deg C, 1 h, 2.) CH₂Cl₂, 25 deg C, 30 min

5: 90 percent / DMAP / CH₂Cl₂ / 0.33 h / 25 °C

6: 100 percent / camphorsulfonic acid (CSA) / methanol

7: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

8: 95 percent / MeONa / methanol / 2 h / 25 °C

9: 80 percent / DMAP / CH₂Cl₂ / 2 h / 0 °C

10: 95 percent / NaH / diethyl ether / 12 h / 45 °C

With 2,6-dimethylpyridine; dmap; sodium hydroxide; borane-THF; camphor-10-sulfonic acid; dihydrogen peroxide; sodium methylate; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1039/c39920001118