Benzyl-[(R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-but-3-enyl]-carbamic acid benzyl ester

Base Information

Chemical Name:Benzyl-[(R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-but-3-enyl]-carbamic acid benzyl ester
CAS No.:899431-87-9
Molecular Formula:C₃₃H₃₇NO₇
Molecular Weight:559.659
Hs Code.:

Synonyms:Benzyl-[(R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-but-3-enyl]-carbamic acid benzyl ester

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Chemical Property of Benzyl-[(R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-but-3-enyl]-carbamic acid benzyl ester

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Technology Process of Benzyl-[(R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-but-3-enyl]-carbamic acid benzyl ester

There total 7 articles about Benzyl-[(R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-but-3-enyl]-carbamic acid benzyl ester 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:

: Benzyl-[(S)-1-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

: 899431-87-9
Benzyl-[(R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-but-3-enyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 2.90 g / sodium metaperiodate / acetone; H₂O / 6 h

2: tetrahydrofuran / 1 h / -50 °C

With sodium periodate; In tetrahydrofuran; water; acetone; 2: Grignard reaction;
DOI:10.1021/jo0601617

Reference yield:

: 899431-69-7
3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-benzyl-N-benzoxycarbonylamino)-α-D-gluco-6-eno-hepta-1,4-furanose

: 899431-87-9
Benzyl-[(R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-but-3-enyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: NMO; potassium osmate / acetone; H₂O / 12 h / 20 °C

2: 2.90 g / sodium metaperiodate / acetone; H₂O / 6 h

3: tetrahydrofuran / 1 h / -50 °C

With potassium osmate(VI); sodium periodate; N-methyl-2-indolinone; In tetrahydrofuran; water; acetone; 3: Grignard reaction;
DOI:10.1021/jo0601617

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 899431-87-9
Benzyl-[(R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-but-3-enyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / sodium bicarbonate / methanol; H₂O / 3 h / 0 °C

2: NMO; potassium osmate / acetone; H₂O / 12 h / 20 °C

3: 2.90 g / sodium metaperiodate / acetone; H₂O / 6 h

4: tetrahydrofuran / 1 h / -50 °C

With potassium osmate(VI); sodium periodate; N-methyl-2-indolinone; sodium hydrogencarbonate; In tetrahydrofuran; methanol; water; acetone; 4: Grignard reaction;
DOI:10.1021/jo0601617