(5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene

Base Information

Chemical Name:(5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene
CAS No.:213255-06-2
Molecular Formula:C₂₇H₃₃NO₅
Molecular Weight:451.563
Hs Code.:

Synonyms:(5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene

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Chemical Property of (5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene

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Technology Process of (5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene

There total 13 articles about (5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene 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

: 213255-06-2
(5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene

Guidance literature:: Multi-step reaction with 12 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

With pyridine; 1H-imidazole; sodium hypochlorite; lithium aluminium tetrahydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; tetrapropylammonium perruthennate; In tetrahydrofuran; 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;
DOI:10.1021/jo9810563

Reference yield:

: 100-39-0
benzyl bromide

: 213255-06-2
(5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene

Guidance literature:: Multi-step reaction with 13 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

With pyridine; 1H-imidazole; sodium hypochlorite; lithium aluminium tetrahydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; tetrapropylammonium perruthennate; In tetrahydrofuran; 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;
DOI:10.1021/jo9810563

Reference yield:

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

: 213255-06-2
(5S,5aS,9aR,9bS)-5-Benzyloxy-5a-benzyloxymethyl-7,7,9b-trimethyl-1,5,5a,9,9a,9b-hexahydro-4H-2,6,8-trioxa-3-aza-cyclopenta[a]naphthalene

Guidance literature:: Multi-step reaction with 10 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

With pyridine; 1H-imidazole; sodium hypochlorite; N-methyl-2-indolinone; camphor-10-sulfonic acid; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; tetrapropylammonium perruthennate; In tetrahydrofuran; 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;
DOI:10.1021/jo9810563