(S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime

Base Information

• Chemical Name: (S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime
• CAS No.: 213255-14-2
• Molecular Formula: C₂₇H₃₅NO₅
• Molecular Weight: 453.579
• Mol file: 213255-14-2.mol

Synonyms:(S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime

Chemical Property of (S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime

There total 13 articles about (S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime 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: 73.0%

(S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde (213255-12-0) → (S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime (213255-14-2)

Guidance literature:

With pyridine; hydroxylamine hydrochloride;

DOI:10.1021/jo9810563

Reference yield:

methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside (132487-16-2) → (S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime (213255-14-2)

Guidance literature:

Multi-step reaction with 10 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

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

DOI:10.1021/jo9810563

Reference yield:

2-Deoxy-D-ribose (533-67-5) → (S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde oxime (213255-14-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: HCl

2.1: NaH

3.1: m-CPBA; BF₃*Et₂O

4.1: LiAlH₄

5.1: imidazole

6.1: Swern oxidation

7.1: LDA / tetrahydrofuran / -78 °C

7.2: tetrahydrofuran / 0.17 h / -78 °C

8.1: DIBAL-H

9.1: CSA

10.1: TBAF / tetrahydrofuran

11.1: 77 percent / NMO / TPAP

12.1: 73 percent / NH₂OH*HCl; pyridine

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; tetrapropylammonium perruthennate; In tetrahydrofuran; 1.1: Cyclization / 2.1: Etherification / 3.1: Oxidation / 4.1: Reduction / 5.1: silylation / 6.1: Swern oxidation / 7.1: Metallation / 7.2: Addition / 8.1: Reduction / 9.1: Cyclization / 10.1: desilylation / 11.1: Oxidation / 12.1: Condensation;

DOI:10.1021/jo9810563

upstream raw materials:

(S)-3-Benzyloxy-3-((4S,5R)-4-benzyloxymethyl-5-isopropenyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionaldehyde

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

2-Deoxy-D-ribose

benzyl bromide

Downstream raw materials:

(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

(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

Refernces