(4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine

Base Information

Chemical Name:(4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine
CAS No.:213255-15-3
Molecular Formula:C₃₉H₆₄O₆Si₂
Molecular Weight:685.105
Hs Code.:

(4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine

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Chemical Property of (4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine

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Technology Process of (4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine

There total 16 articles about (4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine 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:

: 132487-16-2
methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside

: 213255-15-3
(4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine

Guidance literature:: Multi-step reaction with 15 steps

1.1: m-CPBA; BF₃*Et₂O

2.1: LiAlH₄

3.1: imidazole

4.1: Swern oxidation

5.1: LDA / tetrahydrofuran / -78 °C

5.2: tetrahydrofuran / 0.17 h / -78 °C

6.1: DIBAL-H

7.1: CSA

8.1: TBAF / tetrahydrofuran

9.1: 77 percent / NMO / TPAP

10.1: 73 percent / NH₂OH*HCl; pyridine

11.1: NaOCl / H₂O / 0.25 h / 0 °C

12.1: triethylamine / 3 h / 20 °C

13.1: H₂; B(OH)3 / Raney Ni (W₂) / methanol; H₂O

14.1: NaBH₄

15.1: imidazole

With pyridine; 1H-imidazole; sodium hypochlorite; sodium tetrahydroborate; lithium aluminium tetrahydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; boric acid; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; tetrapropylammonium perruthennate; Raney Ni (W₂); In tetrahydrofuran; methanol; water; 1.1: Oxidation / 2.1: Reduction / 3.1: silylation / 4.1: Swern oxidation / 5.1: Metallation / 5.2: Addition / 6.1: Reduction / 7.1: Cyclization / 8.1: desilylation / 9.1: Oxidation / 10.1: Condensation / 11.1: Oxidation / 12.1: Cycloaddition / 13.1: Hydrogenolysis / 14.1: Reduction / 15.1: silylation;
DOI:10.1021/jo9810563

Reference yield:

: 100-39-0
benzyl bromide

: 213255-15-3
(4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine

Guidance literature:: Multi-step reaction with 16 steps

1.1: NaH

2.1: m-CPBA; BF₃*Et₂O

3.1: LiAlH₄

4.1: imidazole

5.1: Swern oxidation

6.1: LDA / tetrahydrofuran / -78 °C

6.2: tetrahydrofuran / 0.17 h / -78 °C

7.1: DIBAL-H

8.1: CSA

9.1: TBAF / tetrahydrofuran

10.1: 77 percent / NMO / TPAP

11.1: 73 percent / NH₂OH*HCl; pyridine

12.1: NaOCl / H₂O / 0.25 h / 0 °C

13.1: triethylamine / 3 h / 20 °C

14.1: H₂; B(OH)3 / Raney Ni (W₂) / methanol; H₂O

15.1: NaBH₄

16.1: imidazole

With pyridine; 1H-imidazole; sodium hypochlorite; sodium tetrahydroborate; lithium aluminium tetrahydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; boric acid; sodium hydride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; tetrapropylammonium perruthennate; Raney Ni (W₂); In tetrahydrofuran; methanol; water; 1.1: Etherification / 2.1: Oxidation / 3.1: Reduction / 4.1: silylation / 5.1: Swern oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Reduction / 8.1: Cyclization / 9.1: desilylation / 10.1: Oxidation / 11.1: Condensation / 12.1: Oxidation / 13.1: Cycloaddition / 14.1: Hydrogenolysis / 15.1: Reduction / 16.1: silylation;
DOI:10.1021/jo9810563

Reference yield:

: 139870-42-1
(3S,4R)-3,5-bis(benzyloxy)pentane-1,4-diol

: 213255-15-3
(4aR,5R,6S,8S,8aS)-8-Benzyloxy-8a-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxine

Guidance literature:: Multi-step reaction with 13 steps

1.1: imidazole

2.1: Swern oxidation

3.1: LDA / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran / 0.17 h / -78 °C

4.1: DIBAL-H

5.1: CSA

6.1: TBAF / tetrahydrofuran

7.1: 77 percent / NMO / TPAP

8.1: 73 percent / NH₂OH*HCl; pyridine

9.1: NaOCl / H₂O / 0.25 h / 0 °C

10.1: triethylamine / 3 h / 20 °C

11.1: H₂; B(OH)3 / Raney Ni (W₂) / methanol; H₂O

12.1: NaBH₄

13.1: imidazole

With pyridine; 1H-imidazole; sodium hypochlorite; sodium tetrahydroborate; N-methyl-2-indolinone; camphor-10-sulfonic acid; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; boric acid; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; tetrapropylammonium perruthennate; Raney Ni (W₂); In tetrahydrofuran; methanol; water; 1.1: silylation / 2.1: Swern oxidation / 3.1: Metallation / 3.2: Addition / 4.1: Reduction / 5.1: Cyclization / 6.1: desilylation / 7.1: Oxidation / 8.1: Condensation / 9.1: Oxidation / 10.1: Cycloaddition / 11.1: Hydrogenolysis / 12.1: Reduction / 13.1: silylation;
DOI:10.1021/jo9810563