(5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-gluco-heptofuranose

Base Information

Chemical Name:(5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-gluco-heptofuranose
CAS No.:1016185-65-1
Molecular Formula:C₂₅H₄₀O₉SSi
Molecular Weight:544.739
Hs Code.:

Synonyms:(5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-gluco-heptofuranose

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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 (5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-gluco-heptofuranose

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Technology Process of (5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-gluco-heptofuranose

There total 8 articles about (5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-gluco-heptofuranose 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: 95.0%

: 1016185-62-8
(5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranose

: 98-59-9
p-toluenesulfonyl chloride

: 1016185-65-1
(5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-gluco-heptofuranose

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1071/CH07002

Reference yield:

: 1016185-59-3
(5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-6,7,8-trideoxy-α-D-gluco-oct-7-enofuranose

: 1016185-65-1
(5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-gluco-heptofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: NaIO₄; OsO₄ / tetrahydrofuran; H₂O / 18 h / 20 °C

2: 1.72 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

3: 95 percent / DMAP / CH₂Cl₂ / 18 h / 20 °C

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1071/CH07002

Reference yield:

: C₁₈H₃₂SiO₇

: 1016185-65-1
(5R)-3-O-acetyl-5-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-gluco-heptofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 1.72 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

2: 95 percent / DMAP / CH₂Cl₂ / 18 h / 20 °C

With dmap; sodium tetrahydroborate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1071/CH07002