tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Base Information

Chemical Name:tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane
CAS No.:310870-41-8
Molecular Formula:C₄₉H₅₂O₅SSi
Molecular Weight:781.1
Hs Code.:

Synonyms:tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

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Chemical Property of tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

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Technology Process of tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

There total 5 articles about tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane 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: 76.0%

: 100-39-0
benzyl bromide

: 310870-40-7
phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside

: 310870-41-8
tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Guidance literature:: phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.25h;

benzyl bromide; In tetrahydrofuran; at 20 ℃; for 20h; Further stages.;
DOI:10.1002/1521-3765(20001002)6:19<3608::AID-CHEM3608>3.0.CO;2-Q

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-Mannose pentaacetate

: 310870-41-8
tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 20 h / 20 °C

2.1: 94 percent / MeONa / methanol / 1 h / 20 °C

3.1: 87 percent / imidazol / tetrahydrofuran / 20 h / 0 °C

4.1: NaH; TBAI / tetrahydrofuran / 0.25 h / 0 °C

4.2: 76 percent / tetrahydrofuran / 20 h / 20 °C

With 1H-imidazole; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/1521-3765(20001002)6:19<3608::AID-CHEM3608>3.0.CO;2-Q

Reference yield:

: 13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5
phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

: 310870-41-8
tert-Butyl-diphenyl-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 94 percent / MeONa / methanol / 1 h / 20 °C

2.1: 87 percent / imidazol / tetrahydrofuran / 20 h / 0 °C

3.1: NaH; TBAI / tetrahydrofuran / 0.25 h / 0 °C

3.2: 76 percent / tetrahydrofuran / 20 h / 20 °C

With 1H-imidazole; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol;
DOI:10.1002/1521-3765(20001002)6:19<3608::AID-CHEM3608>3.0.CO;2-Q