Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside

Base Information

• Chemical Name: Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside
• CAS No.: 119947-94-3
• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.412
• Mol file: 119947-94-3.mol

Synonyms:Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside

Chemical Property of Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside

There total 8 articles about Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside 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: 9.0%

<2R-<2α(R*),6β>>-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-6-methoxy-6-<(phenylmethoxy)methyl>-2H-pyran-3(6H)-one (120052-41-7) → Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside (119947-94-3) + Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-ribo-oct-3-en-2-ulopyranoside (119947-95-4)

Guidance literature:

With potassium tri-sec-butyl-borohydride; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/jo00023a028

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside (119947-94-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) t-BuLi / 1.) THF, -78 to 0 deg C, 4 h, 2.) 0 to 25 deg C, 12 h

2: (n-Bu)4NF / tetrahydrofuran / 12 h / 25 °C

3: 1.) t-BuOOH, VO(acac)2, 2.) Ag₂O / 1.) CH₂Cl₂, 25 deg C, 6 h, 2.) 25 deg C, 24 h

4: K-Selectride / tetrahydrofuran / 0.5 h / -78 °C

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium tri-sec-butyl-borohydride; silver(l) oxide; In tetrahydrofuran;

DOI:10.1021/ja00188a060

Reference yield:

*,R*)>-(2,2-Dimethyl-α-(2-furanyl)-1,3-dioxolan-4-yl)methyl tert-butyldimethylsilyl ether (119947-92-1) → Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside (119947-94-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) t-BuLi / 1.) THF, -78 to 0 deg C, 4 h, 2.) 0 to 25 deg C, 12 h

2: (n-Bu)4NF / tetrahydrofuran / 12 h / 25 °C

3: 1.) t-BuOOH, VO(acac)2, 2.) Ag₂O / 1.) CH₂Cl₂, 25 deg C, 6 h, 2.) 25 deg C, 24 h

4: K-Selectride / tetrahydrofuran / 0.5 h / -78 °C

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium tri-sec-butyl-borohydride; silver(l) oxide; In tetrahydrofuran;

DOI:10.1021/ja00188a060

upstream raw materials:

<2R-<2α(R^*),6β>>-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-6-methoxy-6-<(phenylmethoxy)methyl>-2H-pyran-3(6H)-one

Benzyloxymethyl chloride

*,R^*)>-(2,2-Dimethyl-α-(2-furanyl)-1,3-dioxolan-4-yl)methyl tert-butyldimethylsilyl ether

*,R^*)>-2,2-Dimethyl-α-<5-<(phenylmethoxy)methyl>-2-furanyl>-1,3-dioxolane-4-methanol

Downstream raw materials:

Methyl 3-deoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-manno-2-octulopyranoside cyclic carbonate

Methyl 3-deoxy-3-iodo-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-glycero-α-D-galacto-2-octulopyranoside cyclic carbonate

Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside carbamate