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

Base Information

Chemical Name:Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside carbamate
CAS No.:119947-97-6
Molecular Formula:C₂₀H₂₇NO₇
Molecular Weight:393.437
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 9 articles about Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside carbamate 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:

: 3587-60-8
Benzyloxymethyl chloride

: 119947-97-6
Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside carbamate

Guidance literature:: Multi-step reaction with 5 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

5: 2.) K₂CO₃ / 1.) CH₂Cl₂, 2.) MeOH, H₂O

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium tri-sec-butyl-borohydride; potassium carbonate; silver(l) oxide; In tetrahydrofuran;
DOI:10.1021/ja00188a060

Reference yield:

: [(R)-(5-Benzyloxymethyl-furan-2-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxy]-tert-butyl-dimethyl-silane

: 119947-97-6
Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside carbamate

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

4: 2.) K₂CO₃ / 1.) CH₂Cl₂, 2.) MeOH, H₂O

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; potassium tri-sec-butyl-borohydride; potassium carbonate; silver(l) oxide; In tetrahydrofuran;
DOI:10.1021/ja00188a060

Reference yield:

: 119947-93-2
*,R^*)>-2,2-Dimethyl-α-<5-<(phenylmethoxy)methyl>-2-furanyl>-1,3-dioxolane-4-methanol

: 119947-97-6
Methyl 3,4-dideoxy-7,8-O-(1-methylethylidene)-1-O-(phenylmethyl)-α-D-arabino-oct-3-en-2-ulopyranoside carbamate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 2.) K₂CO₃ / 1.) CH₂Cl₂, 2.) MeOH, H₂O

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; potassium tri-sec-butyl-borohydride; potassium carbonate; silver(l) oxide; In tetrahydrofuran;
DOI:10.1021/ja00188a060